Material for organic electroluminescence device and organic electroluminescence device using the same

ABSTRACT

Provided are an organic electroluminescence device, which: shows high luminous efficiency; is free of any pixel defect; and has a long lifetime, and a material for an organic electroluminescence device for realizing the device. The material for an organic electroluminescence device is a compound of a specific structure having a n-conjugated heteroacene skeleton crosslinked with a carbon atom, nitrogen atom, or oxygen atom. The organic electroluminescence device has one or more organic thin film layers including a light emitting layer between a cathode and an anode, and at least one layer of the organic thin film layers contains the material for an organic electroluminescence device.

CROSS REFERENCE TO RELATED APPLICATION

This application is a continuation application of U.S. application Ser.No. 12/253,627, filed on Oct. 17, 2008, and claims priority to JapanesePatent Application No. 2008-148515, filed on Jun. 5, 2008.

TECHNICAL FIELD

The present invention relates to a material for an organicelectroluminescence device and an organic electroluminescence deviceusing the material, in particular, an organic electroluminescencedevice, which: shows high luminous efficiency; is free of any pixeldefect; and has a long lifetime, and a material for an organicelectroluminescence device for realizing the device.

BACKGROUND ART

An organic electroluminescence device (hereinafter,“electroluminescence” may be abbreviated as “EL”) is a spontaneous lightemitting device which utilizes the principle that a fluorescentsubstance emits light by energy of recombination of holes injected froman anode and electrons injected from a cathode when an electric field isapplied. Since an organic EL device of the laminate type driven under alow electric voltage was reported, many studies have been conducted onorganic EL devices using organic materials as the constituent materials.The devices of the laminate type use tris(8-quinolinolato) aluminum fora light emitting layer and a triphenyldiamine derivative for a holetransporting layer. Advantages of the laminate structure are that theefficiency of hole injection into the light emitting layer can beincreased, that the efficiency of forming exciton which are formed byblocking and recombining electrons injected from the cathode can beincreased, and that exciton formed within the light emitting layer canbe enclosed. As described above, for the structure of the organic ELdevice, a two-layered structure having a hole transporting (injecting)layer and an electron transporting light emitting layer and athree-layered structure having a hole transporting (injecting) layer, alight emitting layer, and an electron transporting (injecting) layer arewell known. To increase the efficiency of recombination of injectedholes and electrons in the devices of the laminate type, the structureof the device and the process for forming the device have been studied.

As the light emitting material of the organic EL device, chelatecomplexes such as tris(8-quinolinolato) aluminum complexes, coumarinederivatives, tetraphenylbutadiene derivatives, distyrylarylenederivatives, and oxadiazole derivatives are known. It is reported thatlight in the visible region ranging from blue light to red light can beobtained by using these light emitting materials, and development of adevice exhibiting color images is expected.

In addition, it has been recently proposed that a phosphorescentmaterial as well as a fluorescent material be utilized in the lightemitting layer of an organic EL device. High luminous efficiency isachieved by utilizing the singlet and triplet states of an excited stateof an organic phosphorescent material in the light emitting layer of anorganic EL device. Upon recombination of an electron and a hole in anorganic EL device, singlet excitons and triplet excitons may be producedat a ratio of 1:3 owing to a difference in spin multiplicity between thesinglet and triplet excitons, so the use of a phosphorescent materialmay achieve luminous efficiency three to four times as high as that of adevice using fluorescence alone.

Patent Documents 1 to 7 are exemplary inventions each describing suchmaterials for an organic EL device.

Patent Document 1 describes a compound using a structure obtained bycrosslinking a terphenylene skeleton with, for example, a carbon atom,nitrogen atom, or oxygen atom as a mother skeleton. The document, whichmainly discloses data indicative of the potential of the compound toserve as a hole transporting material, describes that the compound isused as a host material for a phosphorescent material in a lightemitting layer. However, the description is limited to a redphosphorescent device, and the luminous efficiency of the device is nothigh enough for the device to be put into practical use.

Patent Document 2 describes an indolocarbazole compound having asubstituent on a nitrogen atom or on an aromatic ring. The documentrecommends that the compound be used as a hole transporting material,and describes that a thermally and morphologically stable, thin holetransporting layer can be prepared from the compound. However, thedocument does not describe data indicative of the usefulness of thecompound as a host material or electron transporting material to be usedtogether with a phosphorescent material.

Patent Document 3 describes indolocarbazole compounds each having asubstituent on a nitrogen atom or on an aromatic ring. The documentdiscloses data on a green light emitting device using any one of thosecompounds as a host material for a phosphorescent material in its lightemitting layer. However, a high voltage must be applied to the device todrive the device, and the device shows low luminous efficiency, so thedevice cannot be sufficiently put into practical use.

Patent Document 4 describes indolocarbazole compounds each having asubstituent. The document describes that each of the compounds functionsas a host material for a phosphorescent material in a light emittinglayer. However, each of those compounds is characterized in that thecompound has a dimer or trimer structure through a linking group, andeach of the compounds tends to have a large molecular weight. Thedocument discloses data on a green phosphorescent device using any oneof those compounds, but all the compounds used each have a largemolecular weight of 800 or more. The efficiency with which a materialhaving a large molecular weight is deposited in a vacuum is poor, andthe material may decompose owing to heating for a long time period, sothe material may be insufficient in terms of practical use.

Patent Documents 5 and 6 describe indenofluorene compounds each having asubstituent on an aromatic ring, and describe that each of the compoundsfunctions as a fluorescent material in a light emitting layer. However,none of the documents describes data indicative of the usefulness ofeach of the compounds as a host material or electron transportingmaterial to be used together with a phosphorescent material.

Patent Document 7 describes compounds each using a structure obtained bycrosslinking a terphenylene skeleton with a sulfur atom, boron atom, orphosphorus atom as a mother skeleton. The document describes that eachof those compounds has excellent oxidation resistance, and allows theformation of an organic semiconductor active layer by an applicationmethod. However, the document does not describe data indicative of theusefulness of each of the compounds as a host material or electrontransporting material to be used together with a fluorescent material orphosphorescent material.

-   Patent Document 1: WO 2006/122630-   Patent Document 2: EP 0909787-   Patent Document 3: WO 2007/063796-   Patent Document 4: WO 2007/063754-   Patent Document 5: US 2002/0132134-   Patent Document 6: US 2003/0044646-   Patent Document 7: JP 2008-81494

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

The present invention has been made with a view to solving the aboveproblems, and an object of the present invention is to provide anorganic EL device which: shows high luminous efficiency; is free of anypixel defect; and has a long lifetime, and a material for an organic ELdevice for realizing the device.

Means for Solving the Problems

The inventors of the present invention have made extensive studies witha view to achieving the above object. As a result, the inventors havefound that the above object can be achieved by using a compound having an-conjugated heteroacene skeleton crosslinked with a carbon atom,nitrogen atom, oxygen atom, or sulfur atom as a material for an organicEL device. Thus, the inventors have completed the present invention.

According to one aspect of the present invention, there is provided amaterial for an organic EL device represented by one of the followingformulae (1) and (2).

[In the formulae (1) and (2), X₁ and X₂ each independently represent O,N—R₁, or CR₂R₃, provided that a case where both X₁ and X₂ representCR₂R₃ is excluded.

In the formulae (1) and (2), R₁, R₂, and R₃ each independently representan alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that, when both X₁ and X₂ representN—R₁, at least one R₁ represents a substituted or unsubstituted,monovalent fused aromatic heterocyclic group having a ring formed of 8to 24 atoms.

In the formula (2), n represents 2, 3, or 4, and the materialrepresented by the formula (2) includes a dimer using L₃ as a linkinggroup for n=2, a trimer using L₃ as a linking group for n=3, or atetramer using L₃ as a linking group for n=4.

In the formulae (1) and (2), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formula (1), L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond.

In the formula (2), when n represents 2, L₃ represents a single bond, analkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, when n represents 3, L₃ represents a trivalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, atrivalent silyl group having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalentaromatic heterocyclic group which has 3 to 24 atoms and which is linkedwith the benzene ring c through a carbon-carbon bond, or when nrepresents 4, L₃ represents a tetravalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, tetravalent cycloalkane having aring formed of 3 to 20 carbon atoms, a silicon atom, a substituted orunsubstituted, tetravalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,tetravalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with the benzene ring c through acarbon-carbon bond.

In the formulae (1) and (2), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formula (1), A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when X₁ and X₂ each represent O or CR₂R₃ and both L₁and L₂ represent single bonds, a case where A₁ and A₂ simultaneouslyrepresent hydrogen atoms is excluded.

In the formulae (1) and (2), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (1) and (2), A₁, A₂, L₁, L₂, and L₃ are each free of anycarbonyl group.]

According to another aspect of the present invention, there is providedan organic EL device having one or more organic thin film layersincluding a light emitting layer between a cathode and an anode in whichat least one layer of the organic thin film layers contains a materialfor an organic EL device as a compound having a n-conjugated heteroaceneskeleton crosslinked with a carbon atom, nitrogen atom, oxygen atom, orsulfur atom. A material for an organic EL device represented by theabove formula (1) or (2) is preferably used as the material for anorganic EL device of the present invention.

Further, the material for an organic EL device is effective also as amaterial for an organic electron device such as an organic solar cell,organic semiconductor laser, a sensor using organic matter, or anorganic TFT.

Effects of the Invention

According to the present invention, there can be provided an organic ELdevice which: shows high luminous efficiency; is free of any pixeldefect; and has a long lifetime, and a material for an organic EL devicefor realizing the device.

BEST MODE FOR CARRYING OUT THE INVENTION

A material for an organic EL device of the present invention isrepresented by one of the following general formulae (1) and (2).

[In the formulae (1) and (2), X₁ and X₂ each independently represent O,N—R₁, or CR₂R₃, provided that a case where both X₁ and X₂ representCR₂R₃ is excluded.

In the formulae (1) and (2), R₁, R₂, and R₃ each independently representan alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that, when both X₁ and X₂ representN—R₁, at least one R₁ represents a substituted or unsubstituted,monovalent fused aromatic heterocyclic group having a ring formed of 8to 24 atoms.

In the formula (2), n represents 2, 3, or 4, and the materialrepresented by the formula (2) includes a dimer using L₃ as a linkinggroup for n=2, a trimer using L₃ as a linking group for n=3, or atetramer using L₃ as a linking group for n=4.

In the formulae (1) and (2), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formula (1), L₂ represents a single bond, an alkyl or alkylenegroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms,a substituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond.

In the formula (2), when n represents 2, L₃ represents a single bond, analkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, when n represents 3, L₃ represents a trivalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, atrivalent silyl group having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalentaromatic heterocyclic group which has 3 to 24 atoms and which is linkedwith the benzene ring c through a carbon-carbon bond, or when nrepresents 4, L₃ represents a tetravalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, tetravalent cycloalkane having aring formed of 3 to 20 carbon atoms, a silicon atom, a substituted orunsubstituted, tetravalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,tetravalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with the benzene ring c through acarbon-carbon bond.

In the formulae (1) and (2), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formula (2), A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when X₁ and X₂ each represent O or CR₂R₃ and both L₁and L₂ represent single bonds, a case where A₁ and A₂ simultaneouslyrepresent hydrogen atoms is excluded.

In the formulae (1) and (2), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

When the benzene ring a is substituted by multiple Y₁s, the benzene ringb is substituted by multiple Y₂s, or the benzene ring c is substitutedby multiple Y₃s in the formulae (1) and (2), each of the rings isrepresented as shown below.

In the formulae (1) and (2), A₁, A₂, L₁, L₂, and L₃ are each free of anycarbonyl group.]

The material for an organic EL device represented by the general formula(1) is preferably a material for an organic EL device represented by anyone of the following general formulae (3) to (6) and (11), and thematerial for an organic EL device represented by the general formula (2)is preferably a material for an organic EL device represented by any oneof the following general formulae (7) to (10) and (12).

[In the formulae (3) to (10), R₁, R₂, and R₃ each independentlyrepresent an alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that at least one R₁ in each of theformulae (3) and (7) represents a substituted or unsubstituted,monovalent fused aromatic heterocyclic group having a ring formed of 8to 24 atoms.

In the formulae (7) to (10), n represents 2, 3, or 4, and the materialrepresented by any one of the formulae (7) to (10) includes a dimerusing L₃ as a linking group for n=2, a trimer using L₃ as a linkinggroup for n=3, or a tetramer using L₃ as a linking group for n=4.

In the formulae (3) to (10), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with the benzene ring a through a carbon-carbon bond.

In the formulae (3) to (6), L₂ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with the benzene ring c through a carbon-carbon bond.

In the formulae (7) to (10), when n represents 2, L₃ represents a singlebond, an alkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, when n represents 3, L₃ represents a trivalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, atrivalent silyl group having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalentaromatic heterocyclic group which has 3 to 24 atoms and which is linkedwith the benzene ring c through a carbon-carbon bond, or when nrepresents 4, L₃ represents a tetravalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, tetravalent cycloalkane having aring formed of 3 to 20 carbon atoms, a silicon atom, a substituted orunsubstituted, tetravalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,tetravalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with the benzene ring c through acarbon-carbon bond.

In the formulae (3) to (10), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formulae (3) to (6), A₂ represents a hydrogen atom, a substitutedor unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when both L₁ and L₂ represent single bonds, a casewhere A₁ and A₂ simultaneously represent hydrogen atoms is excluded.

In the formulae (3) to (10), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (3) to (10), A₁, A₂, L₁, L₂, and L₃ are each free of anycarbonyl group.]

In addition, the general formulae (11) and (12) is preferably thefollowing general formulae (13) and (14).

[In the formulae (12) and (14), n represents 2, 3, or 4, and thematerial represented by one of the formulae (12) and (14) includes adimer using L₃ as a linking group for n=2, a trimer using L₃ as alinking group for n=3, or a tetramer using L₃ as a linking group forn=4.

In the formulae (11) to (14), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with the benzene ring a through a carbon-carbon bond.

In the formulae (11) and (13), L₂ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond.

In the formulae (12) and (14), when n represents 2, L₃ represents asingle bond, an alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkylene group having a ring formed of3 to 20 carbon atoms, a divalent silyl group having 2 to 20 carbonatoms, a substituted or unsubstituted, divalent aromatic hydrocarbongroup having a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, divalent aromatic heterocyclic group which has a ringformed of 3 to 24 atoms and which is linked with the benzene ring cthrough a carbon-carbon bond, when n represents 3, L₃ represents atrivalent alkane having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent cycloalkane having a ring formed of 3 to 20carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted, trivalent aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, trivalent aromatic heterocyclic group which has 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, or when n represents 4, L₃ represents a tetravalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, asilicon atom, a substituted or unsubstituted, tetravalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, tetravalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond.

In the formulae (11) to (14), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formulae (12) and (13), A₂ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₂ through acarbon-carbon bond, provided that, when L₂ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₂ represents ahydrogen atom is excluded, and, when both L₁ and L₂ represent singlebonds, a case where A₁ and A₂ simultaneously represent hydrogen atoms isexcluded.

In the formulae (11) to (14), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (11) to (14), A₁, A₂, L₁, L₂, and L₃ are each free ofany carbonyl group.]

In the general formulae (11) to (14), A₁ preferably represents a silylgroup having 3 to 20 carbon atoms, or an aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with L₁through a carbon-carbon bond.

Further, in the general formulae (11) to (14), A₁ preferably representsan aromatic heterocyclic group which is linked with L₁ through acarbon-carbon bond and which is selected from pyridazine, pyrimidine,pyrazine, 1,3,5-triazine, carbazole, dibenzofuran, dibenzothiophene,phenoxazine, phenothiazine, and dihydroacridine.

In the general formulae (1) to (14), specific examples of each group aredescribed below.

Examples of the substituted or unsubstituted aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms represented by Y₁ to Y₃, R₁to R₃, L₁ to L₃, and A₁ and A₂ include residues having correspondingvalencies such as substituted or unsubstituted benzene, naphthalene,biphenyl, terphenyl, fluorene, phenanthrene, triphenylene, perylene,chrysene, fluoranthene, benzofluorene, benzotriphenylene, benzochrysene,and anthracene. Preferred are benzene, naphthalene, biphenyl, terphenyl,fluorene, and phenanthrene.

Examples of the substituted or unsubstituted aromatic hydrocarbon grouphaving a ring formed of 3 to 24 atoms represented by Y₁ to Y₃, R₁ to R₃,L₁ to L₃, and A₁ and A₂ include residues having corresponding valenciessuch as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine,carbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine,and dihydroacridine. Preferred are pyridine, pyridazine, pyrimidine,pyrazine, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, anddihydroacridine. In addition, examples of at least one substituted orunsubstituted, monovalent fused aromatic heterocyclic group having aring formed of 8 to 24 atoms represented by R₁ include aromaticheterocyclic groups each having a fused structure in examples of thearomatic heterocyclic groups.

Examples of the alkyl group, alkylene group, and trivalent ortetravalent alkane, each of which has 1 to 20 carbon atoms representedby Y, Y₁ to Y₃, L₁ to L₃, and R₁ to R₃ include a methyl group, an ethylgroup, a propyl group, an isopropyl group, an n-butyl group, an s-butylgroup, a t-butyl group, an isobutyl group, an n-pentyl group, an n-hexylgroup, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decylgroup, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, ann-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, ann-heptadecyl group, an n-octadecyl group, an neopentyl group, a1-methylpentyl group, a 2-methylpentyl group, a 1-pentylhexyl group, a1-butylpentyl group, a 1-heptyloctyl group, and a 3-methylpentyl groupor groups obtained by allowing those groups to have two to fourvalencies. Preferred are a methyl group, an ethyl group, a propyl group,an isopropyl group, an n-butyl group, an s-butyl group, an isobutylgroup, a t-butyl group, n-pentyl group, an n-hexyl group, an n-heptylgroup, an n-octyl group, an n-nonyl group, an n-decyl group, ann-undecyl group, an n-dodecyl group, an n-tridecyl group, ann-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, ann-heptadecyl group, an n-octadecyl group, an neopentyl group, a1-methylpentyl group, a 1-pentylhexyl group, a 1-butylpentyl group, anda 1-heptyloctyl group.

Examples of the substituted or unsubstituted cycloalkyl group,cycloalkylene group, and trivalent or tetravalent cycloalkane, each ofwhich has a ring formed of 3 to 20 carbon atoms, represented by Y₁ toY₃, L₁ to L₃, R₁ to R₃, and A₁ and A₂ include a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, and groupsobtained by allowing those group to have two to four valencies.Preferred are a cyclobutyl group, a cyclopentyl group, and a cyclohexylgroup.

Examples of the alkoxy group having 1 to 20 carbon atoms and representedby Y₁ to Y₃ include a methoxy group, an ethoxy group, a methoxy group,an i-propoxy group, an n-propoxy group, an n-butoxy group, an s-butoxygroup, and a t-butoxy group. Preferred are a methoxy group, an ethoxygroup, a methoxy group, an i-propoxy group, and an n-propoxy group.

Examples of the silyl group having 1 to 20 carbon atoms represented byY₁ to Y₃, L₁ to L₃, R₁ to R₃, and A₁ and A₂ include a trimethyl silylgroup, a triethyl silyl group, a tributyl silyl group, a trioctyl silylgroup, a triisobutyl silyl group, a dimethylethyl silyl group, adimethylisopropyl silyl group, a dimethylpropyl silyl group, adimethylbutyl silyl group, a dimethyltertiary butyl silyl group, adiethylisopropyl silyl group, a phenyldimethyl silyl group, adiphenylmethyl silyl group, a diphenyl tertiary butyl group, a triphenylsilyl group, and groups obtained by allowing those groups to have two orthree valencies. Preferred are a trimethyl silyl group, a triethyl silylgroup, and a tributyl silyl group.

Examples of the aralkyl group having 7 to 24 carbon atoms represented byY₁ to Y₃, and R₁ to R₃ include a benzyl group, a phenethyl group, and aphenylpropyl group.

Examples of the substituent that can be substituted for the each groupin the general formulae (1) to (14) include alkyl groups each having 1to 10 carbon atoms (such as a methyl group, an ethyl group, a propylgroup, an isopropyl group, an n-butyl group, an s-butyl group, anisobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, ann-heptyl group, an n-octyl group, a hydroxymethyl group, a1-hydroxyethyl group, a 2-hydroxyethyl group, a 2-hydroxyisobutyl group,a 1,2-dihydroxyethyl group, a 1,3-dihydroxyisopropyl group, a2,3-dihydroxy-t-butyl group, a 1,2,3-trihydroxyisopropyl group, a2,3-dihydroxy-t-butyl group, a 1,2,3-trihydroxypropyl group, achloromethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a2-chloroisobutyl group, a 1,2-dichloroethyl group, a1,3-dichloroisopropyl group, a 2,3-dichloro-t-butyl group, a1,2,3-trichloropropyl group, a bromomethyl group, a 1-bromoethyl group,a 2-bromoethyl group, a 2-bromoisobutyl group, a 1,2-dibromoethyl group,a 1,3-dibromoisopropyl group, a 2,3-dibromo-t-butyl group, a1,2,3-tribromopropyl group, a iodomethyl group, a 1-iodoethyl group, a2-iodoethyl group, a 2-iodoisobutyl group, a 1,2-diiodoethyl group, a1,3-diiodoisopropyl group, a 2,3-diiodo-t-butyl group, a1,2,3-triiodopropyl group, an aminomethyl group, a 1-aminoethyl group, a2-aminoethyl group, a 2-aminoisobutyl group, a 1,2-diaminoethyl group, a1,3-diaminoisopropyl group, a 2,3-diamino-t-butyl group, a1,2,3-triaminopropyl group, a cyanomethyl group, a 1-cyanoethyl group, a2-cyanoethyl group, a 2-cyanoisobutyl group, a 1,2-dicyanoethyl group,1,3-dicyanoisopropyl group, a 2,3-dicyano-t-butyl group, a1,2,3-tricyanopropyl group, a nitromethyl group, a 1-nitroethyl group, a2-nitroethyl group, a 2-nitroisobutyl group, a 1,2-dinitroethyl group, a1,3-dinitroisopropyl group, a 2,3-dinitro-t-butyl group, and a1,2,3-trinitropropyl group), cycloalkyl groups each having a ring formedof 3 to 40 carbon atoms (such as a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexylgroup, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group,and a 2-norbornyl group), alkoxy groups each having 1 to 6 carbon atoms(such as an ethoxy group, a methoxy group, an i-propoxy group, ann-propoxy group, an s-butoxy group, a t-butoxy group, a pentoxy group,and a hexyloxy group), cycloalkoxy groups each having a ring formed of 3to 10 carbon atoms (such as a cyclopentoxy group and a cyclohexyloxygroup), aromatic hydrocarbon groups each having a ring formed of 6 to 40carbon atoms, aromatic heterocyclic groups having a ring formed of 3 to40 atoms, amino groups substituted with aromatic hydrocarbon groupshaving a ring formed of 6 to 40 carbon atoms, ester groups havingaromatic hydrocarbon groups having a ring formed of 6 to 40 carbonatoms, an ester group, cyano group, nitro group, and halogen atom, eachof which has an alkyl group having 1 to 6 carbon atoms.

Of those, alkyl groups each having 1 to 6 carbon atoms, a phenyl group,a pyridyl group, a carbazolyl group, and a dibenzofuranyl group arepreferred and the number of substituents is preferably 1 or 2.

In the material for an organic EL device represented by the generalformula (2), (7) to (10), (12), or (14), n preferably represents 2.

In the general formula (1), (3) to (6), (11), or (13), the total numberof the substituents represented by Y₁, Y₂, and Y₂ is preferably 3 orless, and the total number of the substituents represented by Y₁, Y₂,and Y₃ in the structure of [ ]_(n) in the general formula (2), (7) to(10), (12), or (14) is preferably 3 or less.

In the general formula (1) or (2), X₁ and X₂ are each represented byN—R₁. N—R₁ of X₁ and N—R₁ of X₂ may be preferably different from eachother.

Specific examples of the material for an organic EL device representedby any one of the general formulae (1) to (14) of the present inventionare shown below. However, the present invention is not limited to theseexemplified compounds.

Next, an organic EL device of the present invention will be described.

The organic EL device of the present invention has one or more organicthin film layers including a light emitting layer between a cathode andan anode, and at least one layer of the organic thin film layerscontains a material for an organic EL device serving as a compoundhaving a n-conjugated heteroacene skeleton crosslinked with a carbonatom, nitrogen atom, oxygen atom, or sulfur atom. Specific examples ofthe n-conjugated heteroacene skeleton are shown below.

Indenofluorene (Crosslinked with a Carbon Atom)

Indolocarbazole (Crosslinked with a Nitrogen Atom)

Benzofuranodibenzofuran (Crosslinked with an Oxygen Atom)

Benzothiophenodibenzothiophene (Crosslinked with a Sulfur Atom)

In addition to the foregoing, a n-conjugated heteroacene skeletoncrosslinked with a combination of two or more of a carbon atom, anitrogen atom, an oxygen atom, and a sulfur atom is also permitted.Specific examples of the n-conjugated heteroacene skeleton are shownbelow.

In addition, the above-mentioned material for an organic EL device ofthe present invention is preferably used as the material for an organicEL device.

The organic EL device may have an electron transporting layer betweenthe light emitting layer and the cathode, and the electron transportinglayer may contain the material for an organic EL device. Further, boththe light emitting layer and the electron transporting layer eachpreferably contain the material for an organic EL device.

Alternatively, the organic EL device may have a hole transporting layerbetween the light emitting layer and the anode, and the holetransporting layer may contain the material for an organic EL device.

Further, the material for an organic EL device of the present inventionis preferably incorporated into at least the light emitting layer. Whenthe material is used in the light emitting layer, the lifetime of theorganic EL device can be lengthened. When the material is used in theelectron transporting layer or the electron injecting layer, the voltageat which the device is driven can be reduced. The material is preferablyincorporated into each of two or more layers including the lightemitting layer and the electron transporting layer or the electroninjecting layer at the same time because both the reduced voltage andthe lengthened lifetime can be achieved.

In particular, the light emitting layer as well as the electrontransporting layer or electron injecting layer preferably contains, as ahost material, the material for an organic EL device serving as acompound having a n-conjugated heteroacene skeleton crosslinked with acarbon atom, nitrogen atom, oxygen atom, or sulfur atom, or morepreferably contains, as a host material, a material for an organic ELdevice represented by any one of the following general formulae (15) to(22).

[In the formulae (15) to (18), X₃, X₄, X₅, and X₆ each independentlyrepresent O, S, N—R₁, or CR₂R₃.

In the formulae (15) to (18), R₁, R₂, and R₃ each independentlyrepresent an alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, an aralkyl group having 7 to 24 carbon atoms, a silyl grouphaving 3 to 20 carbon atoms, a substituted or unsubstituted aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted aromatic heterocyclic group having a ringformed of 3 to 24 atoms, provided that, when both X₃ and X₄, or both X₅and X₆, represent N—R₁, at least one R₁ represents a substituted orunsubstituted, monovalent fused aromatic heterocyclic group having aring formed of 8 to 24 atoms.

In the formulae (16) and (18), n represents 2, 3, or 4, and the materialrepresented by one of the formulae (16) and (18) includes a dimer usingL₃ as a linking group for n=2, a trimer using L₃ as a linking group forn=3, or a tetramer using L₃ as a linking group for n=4.

In the formulae (15) to (18), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formulae (15) and (17), L₂ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond, providedthat, when both X₇ and X₈, both X₉ and X₁₀, or both X₁₁ and X₁₂,represent CR₂R₃ and both L₁ and L₂ represent a substituted orunsubstituted, monovalent or divalent aromatic hydrocarbon group havinga ring formed of 6 to 24 carbon atoms, a case where L₁ and L₂ aresimultaneously linked at para positions with respect to a benzene ring bis excluded.

In the formulae (16) and (18), when n represents 2, L₃ represents asingle bond, an alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkylene group having a ring formed of3 to 20 carbon atoms, a divalent silyl group having 2 to 20 carbonatoms, a substituted or unsubstituted, divalent aromatic hydrocarbongroup having a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, divalent aromatic heterocyclic group which has a ringformed of 3 to 24 atoms and which is linked with the benzene ring cthrough a carbon-carbon bond, when n represents 3, L₃ represents atrivalent alkane having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent cycloalkane having a ring formed of 3 to 20carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted, trivalent aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, trivalent aromatic heterocyclic group which has 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, or when n represents 4, L₃ represents a tetravalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, asilicon atom, a substituted or unsubstituted, tetravalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, tetravalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond, provided that, when both X₇and X₈, both X₉ and X₁₀, or both X₁₁ and X₁₂, represent CR₂R₃ and bothL₁ and L₃ represent a substituted or unsubstituted, monovalent,divalent, trivalent, or tetravalent aromatic hydrocarbon group having aring formed of 6 to 24 carbon atoms, a case where L₁ and L₃ aresimultaneously linked at para positions with respect to the benzene ringb is excluded.

In the formulae (15) to (18), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formulae (15) and (17), A₂ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₂ through acarbon-carbon bond, provided that, when L₂ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₂ represents ahydrogen atom is excluded, and, when X₇ and X₈, X₉ and X₁₀, or X₁₁ andX₁₂, each represent O, S, or CR₂R₃ and both L₁ and L₂ represent singlebonds, a case where A₁ and A₂ simultaneously represent hydrogen atoms isexcluded.

In the formulae (15) to (18), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (15) to (18), A₁, A₂, L₁, L₂, and L₃ are each free ofany carbonyl group.]

[In the formulae (20) and (22), n represents 2, 3, or 4, and thematerial represented by one of the formulae (20) and (22) includes adimer using L₃ as a linking group for n=2, a trimer using L₃ as alinking group for n=3, or a tetramer using L₃ as a linking group forn=4.

In the formulae (19) to (22), L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond.

In the formulae (19) and (21), L₂ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring c through a carbon-carbon bond.

In the formulae (20) and (22), when n represents 2, L₃ represents asingle bond, an alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkylene group having a ring formed of3 to 20 carbon atoms, a divalent silyl group having 2 to 20 carbonatoms, a substituted or unsubstituted, divalent aromatic hydrocarbongroup having a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, divalent aromatic heterocyclic group which has a ringformed of 3 to 24 atoms and which is linked with the benzene ring cthrough a carbon-carbon bond, when n represents 3, L₃ represents atrivalent alkane having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent cycloalkane having a ring formed of 3 to 20carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted, trivalent aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, trivalent aromatic heterocyclic group which has 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, or when n represents 4, L₃ represents a tetravalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, asilicon atom, a substituted or unsubstituted, tetravalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, tetravalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond.

In the formulae (19) to (22), A₁ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₁ through acarbon-carbon bond, provided that, when L₁ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₁ represents ahydrogen atom is excluded.

In the formulae (19) and (21), A₂ represents a hydrogen atom, asubstituted or unsubstituted cycloalkyl group having a ring formed of 3to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or an aromatic heterocyclic group whichhas a ring formed of 3 to 24 atoms and which is linked with L₂ through acarbon-carbon bond, provided that, when L₂ represents an alkyl oralkylene group having 1 to 20 carbon atoms, a case where A₂ represents ahydrogen atom is excluded, and, when both L₁ and L₂ represent singlebonds, a case where A₁ and A₂ simultaneously represent hydrogen atoms isexcluded.

In the formulae (19) to (22), Y₁, Y₂, and Y₃ each represent an alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstitutedcycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup which has a ring formed of 3 to 24 atoms and which is linked withthe benzene ring a, b, or c through a carbon-carbon bond, the number ofeach of Y₁ and Y₃ is 0, 1, 2, or 3, and the number of Y₂ is 0, 1, or 2.

In the formulae (19) to (22), A₁, A₂, L₁, L₂, and L₃ are each free ofany carbonyl group.]

Examples of the respective groups represented by Y₁ to Y₃, R₁ to R₃, L₁to L₃, and A₁ and A₂ in the general formulae (15) to (22), and examplesof the substituents for the groups include examples similar to thoselisted for the general formulae (1) to (14).

Specific examples of the material for an organic EL device representedby any one of the general formulae (15) to (22) of the present inventionare shown below. However, the present invention is not limited to theseexemplified compounds.

A multi-layer type organic EL device is obtained by laminating multiplelayers; for example, the device is formed of an anode, a holetransporting layer (a hole injecting layer), a light emitting layer, anda cathode, of an anode, a light emitting layer, an electron transportinglayer (an electron injecting layer), and a cathode, of an anode, a holetransporting layer (a hole injecting layer), a light emitting layer, anelectron transporting layer (an electron injecting layer), and acathode, or of an anode, a hole transporting layer (a hole injectinglayer), a light emitting layer, a hole barrier layer, an electrontransporting layer (an electron injecting layer), and a cathode.

In the organic EL device of the present invention, the light emittinglayer preferably contains the material for an organic EL device as ahost material. In addition, it is preferred that the light emittinglayer be composed of a host material and a phosphorescent material, andthe host material be the material for an organic EL device.

In addition, the material for an organic EL device may be a hostmaterial to be used together with a phosphorescent material, or may bean electron transporting material to be used together with aphosphorescent material. The material has a triplet energy gap ofpreferably 2.2 to 3.2 eV, or more preferably 2.5 to 3.2 eV.

The phosphorescent material is preferably a compound containing iridium(Ir), osmium (Os), ruthenium (Ru), or platinum (Pt) because the compoundhas a high phosphorescent quantum yield, and can additionally improvethe external quantum efficiency of the light emitting device. Thematerial is more preferably a metal complex such as an iridium complex,an osmium complex, a ruthenium complex, or a platinum complex. Of those,the iridium complex and the platinum complex are still more preferable,and an orthometalated iridium complex is most preferable. Specificexamples of the metal complex such as an iridium complex, an osmiumcomplex, a ruthenium complex, or a platinum complex are shown below.

In addition, the organic EL device of the present invention ispreferably such that the light emitting layer contains a host materialand a phosphorescent material, and contains a metal complex having alocal maximum luminous wavelength of 500 nm or less. Further, thematerial of the present invention can be used together with afluorescent dopant. The material can be used together with a blue,green, or red fluorescent dopant. In particular, the material can bemore preferably used together with the blue or green fluorescent dopant.Further, the material can be preferably used also as an electrontransporting material for a fluorescent organic EL device.

The organic EL device of the present invention preferably has areductive dopant in an interfacial region between the cathode and anorganic thin layer (for example, an electron injecting layer or a lightemitting layer). Examples of the reductive dopant include at least onekind selected from an alkali metal, an alkali metal complex, an alkalimetal compound, an alkaline earth metal, an alkaline earth metalcomplex, an alkaline earth metal compound, a rare earth metal, a rareearth metal complex, and a rare earth metal compound.

Preferred examples of the alkali metal include an alkali metal having awork function of 2.9 eV or less, such as Na having a work function of2.36 eV, K having a work function of 2.28 eV, Rb having a work functionof 2.16 eV, and Cs having a work function of 1.95 eV. Of those, K, Rb,and Cs are more preferable, Rb or Cs is still more preferable, and Cs ismost preferable.

Preferred examples of the alkali earth metal include an alkali earthmetal having a work function of 2.9 eV or less, such as Ca having a workfunction of 2.9 eV, Sr having a work function of 2.0 to 2.5 eV, and Bahaving a work function of 2.52 eV.

Preferred examples of the rare earth metal include a rare earth metalhaving a work function of 2.9 eV or less, such as Sc, Y, Ce, Tb, and Yb.

Of those metals, a preferable metal has a particularly high reductiveability, so improvement of light emission intensity and long life oforganic EL device can be attained by adding a relatively small amount ofthe metal to an electron injecting region.

Examples of the alkali metal compound include an alkali oxide such asLi₂O, Cs₂O, or K₂O, and an alkali halide such as LiF, NaF, CsF, or KF.Of those, LiF, Li₂O, or NaF is preferable.

Examples of the alkali earth metal compound include BaO, SrO, CaO, andmixtures thereof such as Ba_(m)Sr_(1-m)O (0<m<1) and Ba_(m)Ca_(1-m)O(0<m<1). Of those, BaO, SrO, and CaO are preferable.

Examples of the rare earth metal compound include YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. Of those, YbF₃, ScF₃, and TbF₃ arepreferable.

The alkali metal complex, alkali earth metal complex, and rare metalcomplex are not particularly limited as long as they each include as ametal ion at least one of alkali metal ions, alkali earth metal ions,and rare earth metal ions. Meanwhile, preferable examples of a ligandinclude, but not limited to, quinolinol, benzoquinolinol, acridinol,phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole,hydroxydiaryloxadiazole, hydroxydiarylthiadiazole,hydroxyphenylpyridine, hydroxyphenylbenzoimidazole,hydroxybenzotriazole, hydroxyfluborane, bipyridyl, phenanthroline,phthalocyanine, porphyrin, cyclopentadiene, β-diketones, azomethines,and derivatives thereof.

For the addition form of the reductive dopant, it is preferable that thereductive dopant be formed in a shape of a layer or an island in theinterfacial region. A preferable example of the forming method includesa method in which an organic substance which is a light emittingmaterial or an electron injecting material for forming the interfacialregion is deposited at the same time as the reductive dopant isdeposited by a resistant heating deposition method, thereby dispersingthe reductive dopant in the organic substance. The disperseconcentration by molar ratio of the organic compound to the reductivedopant is 100:1 to 1:100, and is preferably 5:1 to 1:5.

In a case where the reductive dopant is formed into the shape of alayer, the light emitting material or electron injecting material whichserves as an organic layer in the interface is formed into the shape ofa layer. After that, the reductive dopant is solely deposited by theresistant heating deposition method to form a layer preferably having athickness of 0.1 to 15 nm.

In a case where the reductive dopant is formed into the shape of anisland, the light emitting material or electron injecting material whichserves as an organic layer in the interface is formed into the shape ofan island. After that, the reductive dopant is solely deposited by theresistant heating deposition method to form an island preferably havinga thickness of 0.05 to 1 nm.

When the organic EL device of the present invention has an electroninjecting layer between the light emitting layer and the cathode, anelectron transporting material to be used in the electron injectinglayer is preferably an aromatic heterocyclic compound containing one ormore heteroatoms in any one of its molecules, or particularly preferablya nitrogen-containing ring derivative.

The nitrogen-containing ring derivative is preferably, for example, anitrogen-containing ring metal chelate complex represented by thefollowing general formula (A).

R² to R⁷ each independently represent a hydrogen atom, a halogen atom,an amino group, a hydrocarbon group each having 1 to 40 carbon atoms, analkoxy group, an aryloxy group, an alkoxycarbonyl group, or aheterocyclic group, each of which may be substituted.

Examples of the halogen atom represented by R² to R⁷ include a fluorineatom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the amino group that may be substituted and represented byR² to R⁷ include an alkylamino group, an arylamino group, and anaralkylamino group. Examples of the alkyl group in the alkylamino groupinclude alkyl groups each having 1 to 40 carbon atoms such as a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonylgroup, an n-decyl group, an n-undecyl group, an n-dodecyl group, ann-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, ann-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, anneopentyl group, a 1-methylpentyl group, a 2-methylpentyl group, a1-pentylhexyl group, a 1-butylpentyl group, a 1-heptyloctyl group, a3-methylpentyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, a iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 1,2-dinitroethylgroup, a 2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.Preferred are alkyl groups each having 1 to 20 carbon atoms and morepreferred are alkyl groups each having 1 to 10 carbon atoms.

Examples of the aryl group in the arylamino group include aryl groupseach having a ring formed of 6 to 40 carbon atoms such as a phenylgroup, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, 4-phenanthryl group, a9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenylgroup, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group,a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, a an m-terphenyl-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group. Preferred are aryl groups each havinga ring formed of 6 to 20 carbon atoms and more preferred are aryl groupseach having a ring formed of 6 to 10 carbon atoms.

Examples of the aralkyl group in the aralkylamino group include aralkylgroups each having 7 to 40 carbon atoms such as a benzyl group, a1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethylgroup, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, aβ-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethylgroup, a 1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group, a1-pyrrolylmethyl group, 2-(1-pyrrolyl)ethyl group, a p-methylbenzylgroup, an m-methylbenzyl group, an o-methylbenzyl group, ap-chlorobenzyl group, an m-chlorobenzyl group, an o-chlorobenzyl group,a p-bromobenzyl group, an m-bromobenzyl group, an o-bromobenzyl group, ap-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzyl group, ap-hydroxybenzyl group, an m-hydroxybenzyl group, an o-hydroxybenzylgroup, a p-aminobenzyl group, an m-aminobenzyl group, an o-aminobenzylgroup, a p-nitrobenzyl group, an m-nitrobenzyl group, an o-nitrobenzylgroup, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzylgroup, a 1-hydroxy-2-phenylisopropyl group, and a1-chloro-2-phenylisopropyl group. Preferred are aralkyl groups eachhaving 7 to 20 carbon atoms and more preferred are aralkyl groups eachhaving 7 to 10 carbon atoms.

Examples of the hydrocarbon groups each having 1 to 40 carbon atomsrepresented by R² to R⁷ include substituted or unsubstituted alkylgroups, alkenyl groups, cycloalkyl groups, aryl groups, and aralkylgroups.

As the alkyl groups, the same examples of the alkyl groups in theabove-mentioned alkylamino group are given, and alkyl groups each having1 to 20 carbon atoms are preferred and alkyl groups each having 1 to 10carbon atoms are more preferred.

Examples of the alkenyl group include alkenyl groups each having 2 to 40carbon atoms such as a vinyl group, an allyl group, a 1-butenyl group, a2-butenyl group, a 3-butenyl group, a 1,3-butanedienyl group, a1-methylvinyl group, a styryl group, a 2,2-diphenylvinyl group, a1,2-diphenylvinyl group, a 1-methylaryl group, a 1,1-dimethylaryl group,a 2-methylallyl group, a 1-phenylallyl group, a 2-phenylallyl group, a3-phenylallyl group, a 3,3-diphenylallyl group, a 1,2-dimethylallylgroup, a 1-phenyl-1-butenyl group, and a 3-phenyl-1-butenyl group.Preferred are alkenyl groups each having 2 to 20 carbon atoms and morepreferred are alkenyl groups each having 2 to 10 carbon atoms.

Examples of the cycloalkyl groups include cycloalkyl groups each havinga ring formed of 3 to 40 carbon atoms such as a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, a4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a1-norbornyl group, and a 2-norbornyl group. Preferred are cycloalkylgroups each having a ring formed of 3 to 10 carbon atoms are preferred.

As the aryl groups, the same examples of the aryl groups in theabove-mentioned arylamino groups are given. Preferred are aryl groupseach having a ring formed of 6 to 20 carbon atoms and more preferred arearyl groups each having a ring formed of 6 to 10 carbon atoms.

As the aralkyl groups, the same examples of the aralkyl groups in theabove-mentioned aralkylamino groups are given. Preferred are aralkylgroups each having 7 to 20 carbon atoms and more preferred are aralkylgroups each having 7 to 10 carbon atoms.

As the alkoxy group that represented by R² to R⁷ and may be substituted,the same examples of the alkyl groups in the above-mentioned alkylaminogroups are given as alkyl group moieties. Preferred are alkoxy groupseach having 1 to 20 carbon atoms and more preferred alkoxy groups having1 to 10 carbon atoms.

As the aryloxy group that represented by R² to R⁷ and may besubstituted, aryl oxy groups each having the same aryl group in theabove-mentioned alkylamino group as an aryl group moiety are given.Preferred are aryl groups each having a ring formed of 6 to 20 carbonatoms and more preferred are aryl groups each having a ring formed of 6to 10 carbon atoms.

As the alkoxycarbonyl group that represented by R² to R⁷ and may besubstituted, alkoxycarbonyl groups each having the same alkyl group inthe above-mentioned alkylamino group as the alkyl group moiety aregiven. Preferred are alkoxycarbonyl groups each having 2 to 20 carbonatoms and more preferred are alkoxycarbonyl groups each having 2 to 10carbon atoms.

The heterocyclic group that represented by R² to R⁷ and may besubstituted is a monocycle or a fused ring. The heterocyclic grouppreferably has a ring formed of 1 to 20 carbon atoms, more preferablyhas a ring formed of 1 to 12 carbon atoms, and still more preferably hasa ring formed of 2 to 10 carbon atoms. The heterocyclic group is anaromatic heterocyclic group having at least one hetero atom selectedform a nitrogen atom, an oxygen atom, a sulfur atom, and selenium atom.Examples of the heterocyclic group include groups derived frompyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene,furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine,pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline,thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline,isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline,cinnoline, pteridine, acridine, phenanthroline, phanazine, tetrazole,benzoimidazole, benzoxazole, benzothiazole, benzotriazole,tetrazaindene, carbazole, and azepine. Preferred are groups derived fromfuran, thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine,quinoline, phthalazine, naphthyridine, quinoxaline, and quinazoline,more preferred are groups derived from furan, thiophene, pyridine, andquinoline, and still more preferred is a quinolinyl group.

M represents aluminum (Al), gallium (Ga), or indium (In). Indium ispreferred.

L⁴ in the formula (A) is a group represented by the following formula(A′) or (A″).

(In the formula, R⁸ to R¹² each independently represent a hydrogen atom,or a substituted or unsubstituted hydrocarbon atoms having 1 to 40carbon atoms, and adjacent groups may form a cyclic structure. Inaddition, R¹³ to R²⁷ each independently represent a hydrogen atom, or asubstituted or unsubstituted hydrocarbon group having 1 to 40 carbonatoms, and adjacent groups may form a cyclic structure.

As the hydrocarbon group having 1 to 40 carbon atoms represented by R⁸to R¹² in the formula (A′) and R¹³ to R²⁷ in the formula (A″), the samespecific examples of R² to R⁷ are given.

In addition, examples of the divalent group in R⁸ to R¹² and R¹³ to R²⁷in the case where adjacent groups form a cyclic structure include atetramethylene group, a pentamethylene group, a hexamethylene group, adiphenylmethane-2,2′-diyl group, a diphenylethane-3,3′-diyl group, anddiphenylpropane-4,4′-diyl group.

Specific examples of the nitrogen-containing ring metal chelate complexrepresented by the formula (A) are shown below. However, the presentinvention is not limited to these exemplified compounds.

A nitrogen-containing heterocyclic derivative is a nitrogen-containingheterocyclic derivative composed of an organic compound having any oneof the following general formulae, and a nitrogen-containing compoundwhich is not a metal complex is also an example of the derivative.Examples of the derivative include a five- or six-membered ringcontaining a skeleton represented by the following formula (a) and aderivative of a structure represented by the following formula (b).

(In the formula (b), X represents a carbon atom or a nitrogen atom, andZ¹ and Z² each independently represent anatomic group capable of forminga nitrogen-containing heterocycle.)

An organic compound having a nitrogen-containing aromatic polycyclecomposed of a five- or six-membered ring is preferable. In the case ofsuch nitrogen-containing aromatic polycycle having multiple nitrogenatoms, a nitrogen-containing aromatic polycyclic aromatic organiccompound having a skeleton obtained by combining the above formulae (a)and (b) or the above formulae (a) and (c) is more preferable.

The nitrogen-containing group of the nitrogen-containing organiccompound is selected from, for example, nitrogen-containing heterocyclicgroups represented by the following general formulae.

(In each of the formulae, R²⁸ represents an aryl group having 6 to 40carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkylgroup having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20carbon atoms, n represents an integer of 0 to 5, and, when n representsan integer of 2 or more, multiple R²⁸s may be identical to or differentfrom each other).

Further, a preferable specific compound is, for example, anitrogen-containing heterocyclic derivative represented by the followingformula.

HAr^(a)-L⁶-Ar^(b)—Ar^(c)

(In the formula, HAr^(a) represents a nitrogen-containing heterocyclewhich has 3 to 40 carbon atoms and which may have a substituent, L⁶represents a single bond, an arylene group which has 6 to 40 carbonatoms and which may have a substituent, or a heteroarylene group whichhas 3 to 40 carbon atoms and which may have a substituent, Ar^(b)represents a divalent aromatic hydrocarbon group which has 6 to 40carbon atoms and which may have a substituent, and Ar^(c) represents anaryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent.)

HAr^(a) is selected from, for example, the following group.

L⁶ is selected from, for example, the following group.

Ar^(c) is selected from, for example, the following group.

Ar^(b) is selected from, for example, the following arylanthranil group.

(In the formulae, R²⁹ to R⁴² each independently represent a hydrogenatom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, analkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to40 carbon atoms, an aryl group which has 6 to 40 carbon atoms and whichmay have a substituent, or a heteroaryl group having 3 to 40 carbonatoms, and Ar^(d) represents an aryl group which has 6 to 40 carbonatoms and which may have a substituent, or a heteroaryl group having 3to 40 carbon atoms.)

In addition, a nitrogen-containing heterocyclic derivative in which R²⁹to R³⁶ in Ar^(b) represented by the above formula each represent ahydrogen atom is preferable.

In addition to the foregoing, the following compound (see JP 09-3448 A)is also suitably used.

(In the formula, R⁴³ to R⁴⁶ each independently represent a hydrogenatom, a substituted or unsubstituted aliphatic group, a substituted orunsubstituted alicyclic group, a substituted or unsubstitutedcarbocyclic aromatic ring group, or a substituted or unsubstitutedheterocyclic group, and X¹ and X² each independently represent an oxygenatom, a sulfur atom, or a dicyanomethylene group.)

In addition to the foregoing, the following compound (see JP 2000-173774A) is also suitably used.

In the formula, R⁴⁷, R⁴⁸, R⁴⁹, and R⁵⁰ represent groups identical to ordifferent from one another, and each represent an aryl group representedby the following formula.

(In the formula, R⁵¹, R⁵², R⁵³, R⁵⁴, and R⁵⁵ represent groups identicalto or different from one another, and each may represent a hydrogenatom, or at least one of them may represent a saturated or unsaturatedalkoxyl, alkyl, amino, or alkylamino group.

Further, a polymer compound containing the nitrogen-containingheterocyclic group or nitrogen-containing heterocyclic derivative isalso permitted.

In addition, the electron transporting layer preferably contains atleast one of the nitrogen-containing heterocyclic derivativesrepresented by the following general formulae (201) to (203).

In the formulae (201) to (203), R⁵⁶ represents a hydrogen atom, an arylgroup which has 6 to 60 carbon atoms and which may have a substituent, apyridyl group which may have a substituent, a quinolyl group which mayhave a substituent, an alkyl group which has 1 to 20 carbon atoms andwhich may have a substituent, or an alkoxy group which has 1 to 20carbon atoms and which may have a substituent, n represents an integerof 0 to 4, R⁵⁷ represents an aryl group which has 6 to 60 carbon atomsand which may have a substituent, a pyridyl group which may have asubstituent, a quinolyl group which may have a substituent, an alkylgroup which has 1 to 20 carbon atoms and which may have a substituent,or an alkoxy group having 1 to 20 carbon atoms, R⁵⁸ and R⁵⁹ eachindependently represent a hydrogen atom, an aryl group which has 6 to 60carbon atoms and which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group which has 1 to 20 carbon atoms and which may have asubstituent, or an alkoxy group which has 1 to 20 carbon atoms and whichmay have a substituent, L⁷ represents a single bond, an arylene groupwhich has 6 to 60 carbon atoms and which may have a substituent, apyridinylene group which may have a substituent, a quinolinylene groupwhich may have a substituent, or a fluorenylene group which may have asubstituent, Ar^(e) represents an arylene group which has 6 to 60 carbonatoms and which may have a substituent, a pyridinylene group which mayhave a substituent, or a quinolinylene group which may have asubstituent, and Ar^(f) represents a hydrogen atom, an aryl group whichhas 6 to 60 carbon atoms and which may have a substituent, a pyridylgroup which may have a substituent, a quinolyl group which may have asubstituent, an alkyl group which has 1 to 20 carbon atoms and which mayhave a substituent, or an alkoxy group which has 1 to 20 carbon atomsand which may have a substituent.

In the formulae, Ar^(g) represents an aryl group which has 6 to 60carbon atoms and which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group which has 1 to 20 carbon atoms and which may have asubstituent, an alkoxy group which has 1 to 20 carbon atoms and whichmay have a substituent, or a group represented by —Ar^(e)—Ar^(f) (Ar^(e)and Ar^(f) each have the same meaning as that described above).

It should be noted that, in the formulae (201) to (203), R⁵⁶ representsa hydrogen atom, an aryl group which has 6 to 60 carbon atoms and whichmay have a substituent, a pyridyl group which may have a substituent, aquinolyl group which may have a substituent, an alkyl group which has 1to 20 carbon atoms and which may have a substituent, or an alkoxy groupwhich has 1 to 20 carbon atoms and which may have a substituent.

The aryl group which has 6 to 60 carbon atoms is preferably an arylgroup having 6 to 40 carbon atoms, or more preferably an aryl grouphaving 6 to 20 carbon atoms, and specific examples of such groupsinclude a phenyl group, a naphthyl group, an anthryl group, aphenanthryl group, a naphthacenyl group, a chrysenyl group, a pyrenylgroup, a biphenyl group, a terphenyl group, a tolyl group, at-butylphenyl group, a (2-phenylpropyl)phenyl group, a fluoranthenylgroup, a fluorenyl group, a monovalent group composed ofspirobifluorene, a perfluorophenyl group, a perfluoronaphthyl group, aperfluoroanthryl group, a perfluorobiphenyl group, a monovalent groupcomposed of 9-phenylanthracene, a monovalent group composed of9-(1′-naphthyl)anthracene, a monovalent group composed of9-(2′-naphthyl)anthracene, a monovalent group composed of6-phenylchrysene, and a monovalent group composed of9-[4-(diphenylamino)phenyl]anthracene; a phenyl group, a naphthyl group,a biphenyl group, a terphenyl group, a 9-(10-phenyl)anthryl group, a9-[10-(1′-naphthyl)]anthryl group, a 9-[10-(2′-naphthyl)]anthryl group,or the like is preferable.

The alkyl group which has 1 to 20 carbon atoms is preferably an alkylgroup having 1 to 6 carbon atoms, and specific examples of such groupinclude a methyl group, an ethyl group, a propyl group, a butyl group, apentyl group, a hexyl group, and a haloalkyl group such as atrifluoromethyl group. An alkyl group having 3 or more carbon atoms maybe linear, cyclic, or branched.

The alkoxy group which has 1 to 20 carbon atoms is preferably an alkoxygroup having 1 to 6 carbon atoms, and specific examples of such groupinclude a methoxy group, an ethoxy group, a propoxy group, a butoxygroup, a pentyloxy group, and a hexyloxy group. An alkoxy group having 3or more carbon atoms may be linear, cyclic, or branched.

Examples of the substituent of each group represented by R⁵⁶ include ahalogen atom, an alkyl group which has 1 to 20 carbon atoms and whichmay have a substituent, an alkoxy group which has 1 to 20 carbon atomsand which may have a substituent, an aryloxy group which has 6 to 40carbon atoms and which may have a substituent, an aryl group which has 6to 40 carbon atoms and which may have a substituent, or a heteroarylgroup which has 3 to 40 carbon atoms and which may have a substituent.

Examples of the halogen atom include fluorine, chlorine, bromine, andiodine.

Examples of the alkyl group which has 1 to 20 carbon atoms, the alkoxygroup which has 1 to 20 carbon atoms, and the aryl group which has 6 to40 carbon atoms include the same examples as those described above.

Examples of the aryloxy group which has 6 to 40 carbon atoms include aphenoxy group and a biphenyloxy group.

Examples of the heteroaryl group which has 3 to 40 carbon atoms includea pyrrolyl group, a furyl group, a thienyl group, a silolyl group, apyridyl group, a quinolyl group, an isoquinolyl group, a benzofurylgroup, an imidazolyl group, a pyrimidyl group, a carbazolyl group, aselenophenyl group, an oxadiazolyl group, and a triazolyl group.

n represents an integer of 0 to 4, or preferably 0 to 2.

In the formula (201), R⁵⁷ represents an aryl group which has 6 to 60carbon atoms and which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group which has 1 to 20 carbon atoms and which may have asubstituent, or an alkoxy group having 1 to 20 carbon atoms.

Specific examples of the respective groups, and preferable carbonnumbers and preferable substituents of those groups are the same asthose described for R⁵⁶.

In the formulae (202) and (203), R⁵⁸ and R⁵⁹ each independentlyrepresent a hydrogen atom, an aryl group which has 6 to 60 carbon atomsand which may have a substituent, a pyridyl group which may have asubstituent, a quinolyl group which may have a substituent, an alkylgroup which has 1 to 20 carbon atoms and which may have a substituent,or an alkoxy group which has 1 to 20 carbon atoms and which may have asubstituent.

Specific examples of the respective groups, and preferable carbonnumbers and preferable substituents of those groups are the same asthose described for R⁵⁶.

In the formulae (201) to (203), L⁷ represents a single bond, an arylenegroup which has 6 to 60 carbon atoms and which may have a substituent, apyridinylene group which may have a substituent, a quinolinylene groupwhich may have a substituent, or a fluorenylene group which may have asubstituent.

The arylene group which has 6 to 60 carbon atoms is preferably anarylene group having 6 to 40 carbon atoms, or more preferably an arylenegroup having 6 to 20 carbon atoms, and specific examples of such groupsinclude divalent groups each formed by removing one hydrogen atom fromthe aryl group described for R⁵⁶. Examples of the substituent of eachgroup represented by L⁷ include the same examples as those described forR⁵⁶.

In addition, L⁷ preferably represents a group selected from the groupconsisting of the following groups.

In the formula (201), Ar^(e) represents an arylene group which has 6 to60 carbon atoms and which may have a substituent, a pyridinylene groupwhich may have a substituent, or a quinolinylene group which may have asubstituent. Examples of the substituents of the respective groupsrepresented by Ar^(e) and Ar^(g) include the same examples as thosedescribed for R⁵⁶.

In addition, Ar^(e) preferably represents a group selected from fusedring groups represented by the following formulae (101) to (110).

In the formulae (101) to (110), each fused ring may be bonded with abonding group composed of a halogen atom, an alkyl group which has 1 to20 carbon atoms and which may have a substituent, an alkoxy group whichhas 1 to 20 carbon atoms and which may have a substituent, an aryloxygroup which has 6 to 40 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent, and, when multiple bonding groups of thiskind are present, the bonding groups may be identical to or differentfrom each other. Specific examples of the respective groups include thesame examples as those described above.

In the formula (110), L′ represents a single bond or a group selectedfrom the group consisting of the following groups.

The formula (103) represented by Ar^(e) is preferably a fused ring grouprepresented by the following formulae (111) to (125).

In the formulae (111) to (125), each fused ring may be bonded with abonding group composed of a halogen atom, an alkyl group which has 1 to20 carbon atoms and which may have a substituent, an alkoxy group whichhas 1 to 20 carbon atoms and which may have a substituent, an aryloxygroup which has 6 to 40 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent, and, when multiple bonding groups of thiskind are present, the bonding groups may be identical to or differentfrom each other. Specific examples of the respective groups include thesame examples as those described above.

In the formula (201), Ar^(f) represents a hydrogen atom, an aryl groupwhich has 6 to 60 carbon atoms and which may have a substituent, apyridyl group which may have a substituent, a quinolyl group which mayhave a substituent, an alkyl group which has 1 to 20 carbon atoms andwhich may have a substituent, or an alkoxy group which has 1 to 20carbon atoms and which may have a substituent.

Specific examples of the respective groups, and preferable carbonnumbers and preferable substituents of those groups are the same asthose described for R⁵⁶.

In the formulae (202) and (203), Ar^(g) represents an aryl group whichhas 6 to 60 carbon atoms and which may have a substituent, a pyridylgroup which may have a substituent, a quinolyl group which may have asubstituent, an alkyl group which has 1 to 20 carbon atoms and which mayhave a substituent, an alkoxy group which has 1 to 20 carbon atoms andwhich may have a substituent, or a group represented by —Ar^(e)—Ar^(f)(Ar^(e) and Ar^(f) each have the same meaning as that described above).

Specific examples of the respective groups, and preferable carbonnumbers and preferable substituents of those groups are the same asthose described for R⁵⁶.

In addition, Ar^(g) preferably represents a group selected from fusedring groups represented by the following formulae (126) to (135).

In the formulae (126) to (135), each fused ring may be bonded with abonding group composed of a halogen atom, an alkyl group which has 1 to20 carbon atoms and which may have a substituent, an alkoxy group whichhas 1 to 20 carbon atoms and which may have a substituent, an aryloxygroup which has 6 to 40 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent, and, when multiple bonding groups of thiskind are present, the bonding groups may be identical to or differentfrom each other. Specific examples of the respective groups include thesame examples as those described above.

In the formula (135), L′ is the same as that described above.

In the formulae (126) to (135), R′ represents a hydrogen atom, an alkylgroup which has 1 to 20 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent. Specific examples of the respective groupsinclude the same examples as those described above.

The general formula (128) represented by Ar^(g) is preferably a fusedring group represented by the following formulae (136) to (158).

In the formulae (136) to (158), each fused ring may be bonded with abonding group composed of a halogen atom, an alkyl group which has 1 to20 carbon atoms and which may have a substituent, an alkoxy group whichhas 1 to 20 carbon atoms and which may have a substituent, an aryloxygroup which has 6 to 40 carbon atoms and which may have a substituent,an aryl group which has 6 to 40 carbon atoms and which may have asubstituent, or a heteroaryl group which has 3 to 40 carbon atoms andwhich may have a substituent, and, when multiple bonding groups of thiskind are present, the bonding groups may be identical to or differentfrom each other. Specific examples of the respective groups include thesame examples as those described above. R′ is the same as that describedabove.

In addition, it is preferred that Ar^(f) and Ar^(g) each independentlyrepresent a group selected from the group consisting of the followinggroups.

Specific examples of the nitrogen-containing heterocyclic derivativesrepresented by the formulae (201) to (203) of the present invention areshown below. However, the present invention is not limited to theseexemplified compounds.

It should be noted that HAr in the following tables represent any one ofthe following parts in the formulae (201) to (203).

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 1-1

2

3

4

5

6

7

8

9

10

11

12

13

14

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 2-1

2

3

4

5

6

7

8

9

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 3-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 4-1

2

3

4

5

6

7

8

9

10 

11 

12 

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 5-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 6-1

2

3

4

5

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 7-1

2

3

4

5

6

7

8

9

10 

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 8-1

2

3

4

5

6

7

8

9

10 

11 

12 

13 

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 9-1

2

3

4

5

6

7

8

9

10 

11 

12 

13 

14 

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 10-1

2

3

4

5

6

7

8

9

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 11-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 12-1

2

3

4

5

6

7

8

9

10 

11 

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 13-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 14-1

2

3

4

5

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 15-1

2

3

4

5

6

7

8

9

10 

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 16-1

2

3

4

5

6

7

8

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 17-1

2

3

4

5

6

7

8

Of those specific examples, (1-1), (1-5), (1-7), (2-1), (3-1), (4-2),(4-6), (7-2), (7-7), (7-8), (7-9), (9-1), (9-7) are particularlypreferred.

In addition, as the nitrogen-containing ring derivative,nitrogen-containing five-membered ring derivative are preferablyexemplified. Examples of the nitrogen-containing five-membered ringinclude an imidazole ring, a triazole ring, a tetrazole ring, anoxadiazole ring, a thiadiazole ring, an oxatriazole ring, and athiatriazole ring. Examples of the nitrogen-containing five-memberedring derivative include a benzoimidazole ring, a benzotriazole ring, apyridinoimidazole ring, a pyrimidinoimidazole ring, and apyridazinoimidazole ring. Particularly preferred is the compoundrepresented by the following general formula (B).

In the general formula (B), L^(B) represents a divalent or more bondinggroup. Examples thereof include a carbon atoms, a silicon atom, anitrogen atom, a boron atom, an oxygen atom, a sulfur atom, metal atoms(for example, a barium atom, a beryllium atom), aromatic hydrocarbonrings, aromatic heterocycles. Of those, preferred are a carbon atom, anitrogen atom, a silicon atom, a boron atom, an oxygen atom, a sulfuratom, aromatic hydrocarbon rings, aromatic heterocyclic groups and morepreferred are a carbon atom, a silicon atom, aromatic hydrocarbon rings,and aromatic heterocyclic groups.

The aromatic hydrocarbon rings and aromatic heterocyclic groupsrepresented by L^(B) may have a substituent. Examples of the substituentinclude alkyl groups, alkenyl groups, aryl groups, amino groups, alkoxygroups, aryloxy groups, acyl groups, alkoxycarbonyl groups,aryloxycarbonyl groups, acyloxy groups, acyloxyamino groups,alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfonylaminogroups, sulfamoyl groups, carbamoyl groups, alkylthio groups, arylthiogroups, sulfonyl groups, halogen atoms, cyano groups, and aromaticheterocyclic groups. Preferred are alkyl groups, aryl groups, alkoxygroups, aryloxy groups, halogen atoms, cyano groups, and aromaticheterocyclic groups, more preferred are alkyl groups, aryl groups,alkoxy groups, aryloxy groups, and aromatic heterocyclic groups, andparticularly preferred are alkyl groups, aryl groups, alkoxy groups, andaromatic heterocyclic groups.

Specific examples of L^(B) include compounds represented below.

X^(B2) in the general formula (B) represents —O—, —S—, or —N(R^(B2))—.R^(B2) represents a hydrogen atom, an aliphatic hydrocarbon group, anaryl group, or a heterocyclic group.

The aliphatic hydrocarbon group represented by R^(B2) is a linear orbranched alkyl group (having preferably 1 to 20, more preferably 1 to12, or particularly preferably 1 to 8 carbon atoms such as a methylgroup, an ethyl group, an isopropyl group, a t-butyl group, an n-octylgroup, an n-decyl group, or an n-hexadecyl group), a cycloalkyl group(having a ring formed of preferably 3 to 10 carbon atoms such as acyclopropyl group, a cyclopentyl group, or a cyclohexyl group), analkenyl group (having preferably 2 to 20, more preferably 2 to 12, orparticularly preferably 2 to 8 carbon atoms such as a vinyl group, anaryl group, a 2-butenyl group, or a 3-pentenyl group), or an alkynylgroup (having preferably 2 to 20, more preferably 2 to 12, orparticularly preferably 2 to 8 carbon atoms such as a propargyl group ora 3-pentynyl group), or is preferably an alkyl group.

The aryl group represented by R^(B2) is a monocycle or a fused ring, andis an aryl group having a ring formed of preferably 6 to 30, morepreferably 6 to 20, or still more preferably 6 to 12 carbon atoms.Examples of such group include a phenyl group, a 2-methylphenyl group, a3-methylphenyl group, a 4-methylphenyl group, a 2-methoxyphenyl group, a3-trifluoromethylphenyl group, a pentafluorophenyl group, a 1-naphthylgroup, and a 2-naphthyl group. Of those, a phenyl group or a2-methylphenyl group is preferable.

The heterocyclic group represented by R^(B2) is a monocycle or a fusedring, and is a heterocyclic group having a ring formed of preferably 1to 20, more preferably 1 to 12, or still more preferably 2 to 10 carbonatoms. The heterocyclic group is an aromatic heterocyclic groupcontaining at least one heteroatom selected from a nitrogen atom, anoxygen atom, a sulfur atom, and a selenium atom. Examples of theheterocyclic group include groups derived from pyrrolidine, piperidine,piperazine, morpholine, thiophene, selenophene, furan, pyrrole,imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine,triazole, triazine, indole, indazole, purine, thiazoline, thiazole,thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline,phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline,pteridine, acridine, phenanthroline, phanazine, tetrazole,benzoimidazole, benzoxazole, benzothiazole, benzotriazole,tetrazaindene, carbazole, azepine, and the like. Preferred are groupsderived from furan, thiophene, pyridine, pyrazine, pyrimidine,pyridazine, triazine, quinoline, phthalazine, naphthyridine,quinoxaline, and quinazoline, more preferred are groups derived fromfuran, thiophene, pyridine, and quinoline, and still more preferred is aquinolinyl group.

The aliphatic hydrocarbon group, the aryl group, and the heterocyclicgroup each represented by R^(B2) may each have a substituent, and thesubstituent is preferably an alkyl group, an alkenyl group, an alkynylgroup, an aryl group, an amino group, an alkoxy group, an aryloxy group,an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, anacyloxy group, an acylamino group, an alkoxycarbonylamino group, anaryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, acarbamoyl group, an alkylthio group, an arylthio group, a sulfonylgroup, a halogen atom, a cyano group, or an aromatic heterocyclic group,more preferably an alkyl group, an aryl group, an alkoxy group, anaryloxy group, a halogen atom, a cyano group, or an aromaticheterocyclic group, still more preferably an alkyl group, an aryl group,an alkoxy group, an aryloxy group, or an aromatic heterocyclic group, orparticularly preferably an alkyl group, an aryl group, an alkoxy group,or an aromatic heterocyclic group.

R^(B2) preferably represents an aliphatic hydrocarbon group, an arylgroup, or a heterocyclic group, more preferably represents an aliphatichydrocarbon group (having preferably 6 to 30, more preferably 6 to 20,or still more preferably 6 to 12 carbon atoms) or an aryl group, orstill more preferably represents an aliphatic hydrocarbon group (havingpreferably 1 to 20, more preferably 1 to 12, or still more preferably 2to 10 carbon atoms).

X^(B2) preferably represents —O— or —N(R^(B2))—, or more preferablyrepresents —N(R^(B2))—.

Z^(B2) represents atoms necessary for forming an aromatic ring. Thearomatic ring formed of Z^(B2) is any one of aromatic hydrocarbon ringsand aromatic heterocyclic rings. Specific examples thereof include abenzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, apyridazine ring, a triazine ring, a pyrrole ring, a furan ring, athiophene ring, a selenophene ring, a tellurophene ring, an imidazolering, a thiazole ring, a selenazole ring, a tellulazole ring, athiadiazole ring, an oxadiazole ring, and a pyrazole ring. Preferred area benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, anda pyridazine ring, more preferred are a benzene ring, a pyridine ring,and a pyrazine ring, still more preferred are a benzene ring andpyridine ring, and particularly preferred is a pyridine ring.

The aromatic ring formed of Z^(B2) may further form a fused ring withany other ring, or may have a substituent. Examples of the substituentinclude the same examples as those described for the substituent of thegroup represented by L^(B), and the substituent is preferably an alkylgroup, an alkenyl group, an alkynyl group, an aryl group, an aminogroup, an alkoxy group, an aryloxy group, an acyl group, analkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, anacylamino group, an alkoxycarbonylamino group, an aryloxycarbonylaminogroup, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, analkylthio group, an arylthio group, a sulfonyl group, a halogen atom, acyano group, or a heterocyclic group, more preferably an alkyl group, anaryl group, an alkoxy group, an aryloxy group, a halogen atom, a cyanogroup, or a heterocyclic group, still more preferably an alkyl group, anaryl group, an alkoxy group, an aryloxy group, or an aromaticheterocyclic group, or particularly preferably an alkyl group, an arylgroup, an alkoxy group, or an aromatic heterocyclic group.

n^(B2) represents an integer of 1 to 4, or preferably 2 or 3.

Of the nitrogen-containing five-membered ring derivatives eachrepresented by the general formula (B), a derivative represented by thefollowing general formula (B′) is more preferable.

In the general formula (B′), R^(B71), R^(B72), and R^(B73) each have thesame meaning as that of R^(B2) in the general formula (B), andpreferable examples of R^(B71), R^(B72), and R^(B73) are also the sameas those of R^(B2).

In the formula, Z^(B71), Z^(B72), and Z^(B73) each have the same meaningas that of Z^(B2) in the general formula (B), and preferable examples ofZ^(B71), Z^(B72), and Z^(B73) are also the same as those of Z^(B2).

In the formula, L^(B71), L^(B72), and Z^(B73) each represent a linkinggroup, and examples of the linking group include examples obtained bymaking the examples of L^(B) in the general formula (B) divalent. Thelinking group is preferably a single bond, a divalent aromatichydrocarbon ring group, a divalent aromatic heterocyclic group, or alinking group composed of a combination of two or more of them, or ismore preferably a single bond. L^(B71), L^(B72), and L^(B73) may eachhave a substituent. Examples of the substituent include the sameexamples as those described for the substituent of the group representedby L^(B) in the general formula (B), and preferable examples of thesubstituent also include the same preferable examples as those describedfor the substituent of the group represented by L^(B) in the generalformula (B).

In the formula, Y^(B) represents a nitrogen atom, a 1,3,5-benzenetriylgroup, or a 2,4,6-triazinetriyl group. The 1,3,5-benzenetriyl group mayhave a substituent at any one of its 2-, 4-, and 6-positions, andexamples of the substituent include an alkyl group, an aromatichydrocarbon ring group, and a halogen atom.

Specific examples of the nitrogen-containing five-membered ringderivative represented by the general formula (B) or (B′) are shownbelow. However, the present invention is not limited to theseexemplified compounds.

A compound of which each of the electron injecting layer and theelectron transporting layer is constituted is, for example, a compoundhaving a structure obtained by combining an electron-deficient,nitrogen-containing five-membered ring skeleton or electron-deficient,nitrogen-containing six-membered ring skeleton and a substituted orunsubstituted indole skeleton, substituted or unsubstituted carbazoleskeleton, or substituted or unsubstituted azacarbazole skeleton as wellas the material for an organic EL device of the present invention. Inaddition, a suitable electron-deficient, nitrogen-containingfive-membered ring skeleton or electron-deficient, nitrogen-containingsix-membered ring skeleton is a molecular skeleton such as a pyridine,pyrimidine, pyrazine, triazine, triazole, oxadiazole, pyrazole,imidazole, quinoxaline, or pyrrole skeleton, or benzimidazole orimidazopyridine obtained when two or more of them fuse with each other.Of those combinations, a preferable combination is, for example, acombination of a pyridine, pyrimidine, pyrazine, or triazine skeletonand a carbazole, indole, azacarbazole, or quinoxaline skeleton. Theabove-mentioned skeleton may be substituted or unsubstituted.

Specific examples of an electron transportable compound are shown below.However, the present invention is not particularly limited to theseexamples.

Each of the electron injecting layer and the electron transporting layermay be of a monolayer structure composed of one or two or more kinds ofthe above materials, or may be of a multi-layered structure composed ofmultiple layers identical to or different from each other incomposition. Materials for those layers each preferably have aπ-electron-deficient, nitrogen-containing heterocyclic group.

In addition, an insulator or semiconductor serving as an inorganiccompound as well as the nitrogen-containing ring derivative ispreferably used as a component of the electron injecting layer. When theelectron injecting layer is constituted of an insulator orsemiconductor, current leakage can be effectively prevented, and theelectron injecting property of the layer can be improved.

As the insulator, at least one metal compound selected from the groupconsisting of alkali metal chalcogenides, alkaline earth metalchalcogenides, alkali metal halides, and alkaline earth metal halides ispreferably used. It is preferable that the electron injecting layer becomposed of the above-mentioned substance such as the alkali metalchalcogenide since the electron injecting property can be furtherimproved. To be specific, preferable examples of the alkali metalchalcogenide include Li₂O, K₂O, Na₂S, Na₂Se, and Na₂O, and preferableexamples of the alkaline earth metal chalcogenide include CaO, BaO, SrO,BeO, BaS, and CaSe. Preferable examples of the alkali metal halideinclude LiF, NaF, KF, LiCl, KCl, and NaCl. Preferable examples of thealkaline earth metal halide include fluorides such as CaF₂, BaF₂, SrF₂,MgF₂, and BeF₂ and halides other than the fluorides.

In addition, examples of the semiconductor include oxides, nitrides, andoxide nitrides containing at least one element selected from the groupconsisting of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb,and Zn used alone or in combination of two or more. It is preferablethat the inorganic compound composing the electron injecting layer forma crystallite or amorphous insulating thin film. When the electroninjecting layer is composed of the insulating thin film described above,a more uniform thin film can be formed, and defects of pixels such asdark spots can be decreased. Examples of the inorganic compound includealkali metal chalcogenides, alkaline earth metal chalcogenides, alkalimetal halides, and alkaline earth metal halides which are describedabove.

In addition, the above-mentioned reducing dopant can be preferablyincorporated into the electron injecting layer in the present invention.

It should be noted that the thickness of each of the electron injectinglayer and the electron transporting layer, which is not particularlylimited, is preferably 1 to 100 nm.

An aromatic amine compound such as an aromatic amine derivativerepresented by a general formula (I) is suitably used in the holeinjecting layer or hole transporting layer (a holeinjecting/transporting layer is also included in this category).

In the general formula (I), Ar¹ to Ar⁴ each represent a substituted orunsubstituted aryl group having a ring formed of 6 to 50 carbon atoms,or a substituted or unsubstituted heteroaryl group having a ring formedof 5 to 50 atoms.

Examples of the substituted or unsubstituted aryl group having 6 to 50ring hydrocarbon atoms include a phenyl group, a 1-naphthyl group, a2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthrylgroup, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthrylgroup, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenylgroup, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenylgroup, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, ap-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-ylgroup, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolylgroup, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, ap-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a4′-methylbiphenylyl group, a 4″-t-butyl-p-terphenyl-4-yl group, afluoranthenyl group, and a fluorenyl group.

Examples of the substituted or unsubstituted heteroaryl group having aring formed of 5 to 50 atoms include a 1-pyrrolyl group, a 2-pyrrolylgroup, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolylgroup, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolylgroup, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group,a 6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furylgroup, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranylgroup, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranylgroup, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranylgroup, a 7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group,a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, an 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl1-indolyl group, a 4-t-butyl1-indolyl group, a2-t-butyl3-indolyl group, and a 4-t-butyl3-indolyl group. Preferred area phenyl group, a naphthyl group, a biphenyl group, an anthranyl group,a phenanthryl group, a pyrenyl group, a chrycenyl group, a fluoranthenylgroup, and a fluorenyl group.

L represents a linking group, and specifically, a substituted orunsubstituted arylene group having a ring formed of 6 to 50 carbonatoms, a substituted or unsubstituted heteroarylene group having a ringformed of 5 to 50 carbon atoms, or a divalent group in which two or morearylene groups or heteroarylene groups are bonded by a single bond, anether bond, a thioether bond, with an alkylene group having 1 to 20carbon atoms, an alkenylene group having 2 to 20 carbon atoms, and anamino group. Examples of the arylene group having a ring formed of 6 to50 carbon atoms include a 1,4-phenylene group, a 1,2-phenylene group, a1,3-phenylene group, a 1,4-naphthylene group, a 2,6-naphthylene group, a1,5-naphthylene group, a 9,10-anthranylene group, a9,10-phenanthrenylene group, a 3,6-phenanthrenylene group,1,6-pyrenylene group, a 2,7-pyrenylene group, a 6,12-chrycenylene group,a 4,4′-biphenylene group, a 3,3′-biphenylene group, a 2,2′-biphenylenegroup, and a 2,7-fluorenylene group. Examples of the arylene grouphaving a ring formed of 5 to 50 atoms include a 2,5-thiophenylene group,a 2,5-silolylene group, and a 2,5-oxadiazolylene group. Preferred are a1,4-phenylene group, a 1,2-phenylene group, a 1,3-phenylene group, a1,4-naphthylene group, a 9,10-anthranylene group, a 6,12-chrysenylenegroup, a 4,4′-biphenylene group, a 3,3′-biphenylene group, a2,2′-biphenylene group, and a 2,7-fluorenylene group. Examples of thearylene group having a ring formed of 5 to 50 atoms include a2,5-thiophenylene group, a 2,5-silolylene group, and a2,5-oxadiazolylene group. Preferred are a 1,4-phenylene group, a1,2-phenylene group, a 1,3-phenylene group, a 1,4-naphthylene group, a9,10-anthranylene group, a 6,12-chrysenylene group, a 4,4′-biphenylenegroup, a 3,3′-biphenylene group, a 2,2′-biphenylene group, and a2,7-fluorenylene group.

In the case where L represents a linking group formed of two or morearylene groups or heteroarylene groups, adjacent arylene groups orheteroarylene groups may be bonded to each other through a divalentgroup to form a ring. Examples of the divalent group forming a ringinclude a tetramethylene group, a pentamethylene group, a hexamethylenegroup, a diphenylmethane-2,2′-diyl group, a diphenyl ethane-3,3′-diylgroup, and a diphenylpropane-4,4′-diyl group.

The substituent of each of Ar¹ to Ar⁴ and L is, for example, asubstituted or unsubstituted aryl group having a ring formed of 6 to 50carbon atoms, a substituted or unsubstituted heteroaryl group having aring formed of 5 to 50 atoms, a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkylgroup having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 50 carbon atoms, a substituted or unsubstitutedaralkyl group having 7 to 50 carbon atoms, a substituted orunsubstituted aryloxy group having a ring formed of 6 to 50 carbonatoms, a substituted or unsubstituted heteroaryloxy group having a ringformed of 5 to 50 atoms, a substituted or unsubstituted arylthio grouphaving a ring formed of 6 to 50 carbon atoms, a substituted orunsubstituted heteroarylthio group having a ring formed of 5 to 50atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to50 carbon atoms, an amino group substituted by a substituted orunsubstituted aryl group having a ring formed of 6 to 50 carbon atoms orby a substituted or unsubstituted heteroaryl group having a ring formedof 5 to 50 atoms, a halogen group, a cyano group, a nitro group, or ahydroxyl group.

Examples of the substituted or unsubstituted aryl group having 6 to 50ring hydrocarbon atoms include a phenyl group, a 1-naphthyl group, a2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthrylgroup, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthrylgroup, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenylgroup, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenylgroup, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, ap-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-ylgroup, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolylgroup, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, ap-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a4′-methylbiphenylyl group, a 4″-t-butyl-p-terphenyl-4-yl group, afluoranthenyl group, and a fluorenyl group.

Examples of the substituted or unsubstituted heteroaryl group having aring formed of 5 to 50 atoms include a 1-pyrrolyl group, a 2-pyrrolylgroup, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolylgroup, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolylgroup, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group,a 6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furylgroup, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranylgroup, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranylgroup, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranylgroup, a 7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group,a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, an 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl1-indolyl group, a 4-t-butyl1-indolyl group, a2-t-butyl3-indolyl group, and a 4-t-butyl3-indolyl group.

Examples of the substituted or unsubstituted alkyl group having 1 to 50carbon atoms include a methyl group, an ethyl group, a propyl group, anisopropyl group, an n-butyl group, an s-butyl group, an isobutyl group,a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group,an n-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted cycloalkyl group having 3to 50 carbon atoms include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a2-norbornyl group.

The substituted or unsubstituted alkoxy group having 1 to 50 carbonatoms is a group represented by —OY. Examples of Y include a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted aralkyl group having 7 to50 carbon atoms include a benzyl group, a 1-phenylethyl group, a2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropylgroup, a phenyl-t-butyl group, an α-naphthylmethyl group, a1-α-naphthylethyl group, a 2-α-naphthylethyl group, a1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, aβ-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethylgroup, a 1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group, a1-pyrolylmethyl group, a 2-(1-pyrrolyl)ethyl group, a p-methylbenzylgroup, an m-methylbenzyl group, an o-methylbenzyl group, ap-chlorobenzyl group, an m-chlorobenzyl group, an o-chlorobenzyl group,a p-bromobenzyl group, an m-bromobenzyl group, an o-bromobenzyl group, ap-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzyl group, ap-hydroxybenzyl group, an m-hydroxybenzyl group, an o-hydroxybenzylgroup, a p-aminobenzyl group, an m-aminobenzyl group, an o-aminobenzylgroup, a p-nitrobenzyl group, an m-nitrobenzyl group, an o-nitrobenzylgroup, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzylgroup, a 1-hydroxy-2-phenylisopropyl group, and a1-chloro-2-phenylisopropyl group.

Examples of the substituted or unsubstituted aryloxy group having a ringformed of 6 to 50 carbon atoms is represented by —OY′. Examples of Y′include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthrylgroup, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthrylgroup, a 9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenylgroup, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a4-pyrenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group,a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-ylgroup, an m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, ap-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenylgroup, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group.

Examples of the substituted or unsubstituted heteroaryloxy group havinga ring formed of 5 to 50 atoms is represented by —OZ′. Examples of Z′include a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 2-indolylgroup, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 3-isoindolylgroup, a 4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group,a 7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 1-phenanthridinyl group, a 2-phenanthridinyl group, a3-phenanthridinyl group, a 4-phenanthridinyl group, a 6-phenanthridinylgroup, a 7-phenanthridinyl group, an 8-phenanthridinyl group, a9-phenanthridinyl group, a 10-phenanthridinyl group, a 1-acridinylgroup, a 2-acridinyl group, a 3-acridinyl group, a 4-acridinyl group, a9-acridinyl group, a 1,7-phenanthrolin-2-yl group, a1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 1-phenoxadinylgroup, a 2-phenoxadinyl group, a 3-phenoxadinyl group, a 4-phenoxadinylgroup, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a4-t-butyl1-indolyl group, a 2-t-butyl3-indolyl group, and a4-t-butyl3-indolyl group.

The substituted or unsubstituted arylthio group having a ring formed of6 to 50 carbon atoms is represented by —SY″. Examples of Y″ include aphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group,a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenylgroup, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group,a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl) phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group.

The substituted or unsubstituted heteroarylthio group having a ringformed of 5 to 50 atoms is represented by —SZ″. Examples of Z″ include a2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinylgroup, a 3-pyridinyl group, a 4-pyridinyl group, a 2-indolyl group, a3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolylgroup, a 7-indolyl group, a 1-isoindolyl group, a 3-isoindolyl group, a4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 1-phenanthridinyl group, a 2-phenanthridinyl group, a3-phenanthridinyl group, a 4-phenanthridinyl group, a 6-phenanthridinylgroup, a 7-phenanthridinyl group, an 8-phenanthridinyl group, a9-phenanthridinyl group, a 10-phenanthridinyl group, a 1-acridinylgroup, a 2-acridinyl group, a 3-acridinyl group, a 4-acridinyl group, a9-acridinyl group, a 1,7-phenanthrolin-2-yl group, a1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 1-phenoxazinylgroup, a 2-phenoxazinyl group, a 3-phenoxazinyl group, a 4-phenoxazinylgroup, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a4-t-butyl1-indolyl group, a 2-t-butyl3-indolyl group, and a4-t-butyl3-indolyl group.

The substituted or unsubstituted alkoxycarbonyl group having 2 to 50carbon atoms is represented by —COOZ. Examples of Z include a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and 1,2,3-trinitropropyl group.

The substituted or unsubstituted aryl group having a ring formed of 6 to50 carbon atoms or an amino group substituted with a substituted orunsubstituted heteroaryl group having a ring formed of 5 to 50 atoms isrepresented by —NPQ. Examples of P and Q include a phenyl group, a1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthrylgroup, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group,a 3-phenanthryl group, 4-phenanthryl group, a 9-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylylgroup, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-ylgroup, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, anm-terphenyl-4-yl group, a an m-terphenyl-3-yl group, an m-terphenyl-2-ylgroup, an o-tolyl group, an m-tolyl group, a p-tolyl group, ap-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4″-t-butyl-p-terphenyl-4-yl group, a 2-pyrrolyl group, a 3-pyrrolylgroup, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a4-pyridinyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolylgroup, a 5-indolyl group, a 6-indolyl group, a 7-indolyl group, a1-isoindolyl group, a 3-isoindolyl group, a 4-isoindolyl group, a5-isoindolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a2-furyl group, a 3-furyl group, a 2-benzofuranyl group, a 3-benzofuranylgroup, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranylgroup, a 7-benzofuranyl group, a 1-isobenzofuranyl group, a3-isobenzofuranyl group, a 4-isobenzofuranyl group, a 5-isobenzofuranylgroup, a 6-isobenzofuranyl group, a 7-isobenzofuranyl group, a2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolylgroup, a 6-quinolyl group, a 7-quinolyl group, an 8-quinolyl group, a1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a5-isoquinolyl group, a 6-isoquinolyl group, a 7-isoquinolyl group, an8-isoquinolyl group, a 2-quinoxalinyl group, a 5-quinoxalinyl group, a6-quinoxalinyl group, a 1-carbazolyl group, a 2-carbazolyl group, a3-carbazolyl group, a 4-carbazolyl group, a 1-phenanthridinyl group, a2-phenanthridinyl group, a 3-phenanthridinyl group, a 4-phenanthridinylgroup, a 6-phenanthridinyl group, a 7-phenanthridinyl group, an8-phenanthridinyl group, a 9-phenanthridinyl group, a 10-phenanthridinylgroup, a 1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group,4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 1-phenoxazinylgroup, a 2-phenoxazinyl group, a 3-phenoxazinyl group, a 4-phenoxazinylgroup, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a4-t-butyl1-indolyl group, a 2-t-butyl3-indolyl group, and a4-t-butyl3-indolyl group.

Specific examples of the compound represented by the general formula (I)are shown below. However, the present invention is not limited to theseexamples.

In addition, an aromatic amine represented by the following generalformula (II) is also suitably used in the formation of the holeinjecting layer or hole transporting layer.

In the general formula (II), the definition of Ar₁ to Ar₃ is the same asthat of Ar¹ to Ar⁴ in the general formula (I). Specific examples of thecompound represented by the general formula (II) are shown below.However, the present invention is not limited to these examples.

The compound of the present invention can be used in each of the holeinjecting layer, the hole transporting layer, the electron injectinglayer, and the electron transporting layer because the compound cantransport both a hole and an electron.

In the present invention, the anode in the organic EL device has thefunction of injecting holes into the hole transporting layer or thelight emitting layer. It is effective that the anode has a work functionof 4.5 eV or greater. Specific examples of the material for the anodeused in the present invention include indium tin oxide alloys (ITO), tinoxide (NESA), gold, silver, platinum, and copper. In addition, as thecathode, a material having a small work function is preferred in view toinject an electron into an electron-injecting layer or a light-emittinglayer. Examples of the cathode material are not particularly limited,and specifically indium, aluminum, magnesium, an magnesium-indium alloy,a magnesium-aluminum alloy, an aluminum-lithium alloy, analuminum-scandium-lithium alloy, and a magnesium-silver alloy may beused.

The method of forming the layers in the organic EL device of the presentinvention is not particularly limited. A conventionally known processsuch as the vacuum vapor deposition process or the spin coating processcan be used. The organic thin film layer which is used in the organic ELdevice of the present invention and includes the compound represented bygeneral formula (1) described above can be formed in accordance with aknown process such as the vacuum vapor deposition process or themolecular beam epitaxy process (MBE process) or, using a solutionprepared by dissolving the compounds into a solvent, in accordance witha coating process such as the dipping process, the spin coating process,the casting process, the bar coating process, or the roll coatingprocess.

The thickness of each layer in the organic thin film layer in theorganic EL device of the present invention is not particularly limited.In general, an excessively thin layer tends to have defects such as pinholes, whereas an excessively thick layer requires a high appliedvoltage to decrease the efficiency. Therefore, a thickness in the rangeof several nanometers to 1 μm is preferable.

EXAMPLES

Next, the present invention is described in detail by way of examples,but the present invention is not limited to the following examples. Notethat, in the synthetic examples below, DMF refers to dimethylformamide,THF refers to tetrahydrofuran, DME refers to dimethoxyethane, NBS refersto N-bromosuccine imide, Ph refers to a phenyl group, AcOEt refers toethyl acetate, and NMP refers to N-methylpyrrolidone.

Synthesis Example 1 Synthesis of Compound No. 1 (1) Synthesis ofCompound 1

1,4-dibromo-2,5-difluorobenzene (49.3 g, 181.5 mmol),2-methoxyphenylboronic acid (66.2 g, 435.6 mmol), and a 2 M aqueoussolution of Na₂CO₃ (363 mL, 726 mmol), DME (360 mL), toluene (360 mL),and Pd[PPh₃]₄ (20.8 g, 18.0 mmol) were loaded into a three-necked flask,and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (500 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 38.5 g in 65% yield.

FD-MS C₂₀H₁₆F₂O₂: theoretical value 326, observed value 326

(2) Synthesis of Compound 2

Compound 1 (36.6 g, 112.2 mmol), NBS (39.9 g, 224 mmol), and DMF (1,000mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at room temperature for 8 hours. After thecompletion of the reaction, the resultant sample was transferred to aseparating funnel, and water (1,000 mL) was charged into the funnel.Then, the mixture was extracted with AcOEt. The resultant sample waspurified by column chromatography, whereby a white solid was obtained inan amount of 38 g in 70% yield.

FD-MS C₂₀H₁₄Br₂F₂O₂: theoretical value 484, observed value 484

(3) Synthesis of Compound 3

Compound 2 (37.2 g, 76.8 mmol), a 1 M solution of BBr₃ in CH₂Cl₂ (180mL, 180 mmol), and CH₂Cl₂ (500 mL) were loaded into a three-neckedflask, and the mixture was stirred under an Ar atmosphere at 0° C. for 8hours. After that, the mixture was left to stand at room temperatureovernight. After the completion of the reaction, the resultant wasneutralized with a saturated aqueous solution of NaHCO₃. The resultantsample was transferred to a separating funnel, and was extracted withCH₂Cl₂. The resultant sample was purified by column chromatography,whereby a white solid was obtained in an amount of 28 g in 80% yield.

FD-MS C₁₈H₁₀Br₂F₂O₂: theoretical value 456, observed value 456

(4) Synthesis of Compound 4

Compound 3 (27.4 g, 60.1 mmol), K₂CO₃ (18.2 g, 132 mmol), and NMP (250mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at 150° C. for 8 hours. After the completion ofthe reaction, the resultant was cooled to room temperature. Theresultant sample was transferred to a separating funnel, and water (500mL) was charged into the funnel. Then, the mixture was extracted withAcOEt. The resultant sample was purified by column chromatography,whereby a white solid was obtained in an amount of 20 g in 80% yield.

FD-MS C₁₈H₈Br₂O₂: theoretical value 416, observed value 416

(5) Synthesis of Compound No. 1

Compound 4 (2.5 g, 6.0 mmol), Compound 5 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 1) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 2.0 g in45% yield.

FD-MS C₅₄H₃₂N₂O₂: theoretical value 740, observed value 740

Synthesis Example 2 Synthesis of Compound No. 11

Compound 6 (2.6 g, 10 mmol), 2-bromodibenzofuran (5.0 g, 20 mmol), CuI(1.9 g, 10 mmol), trans-cyclohexane-1,2-diamine (3.4 g, 30 mmol), K₃PO₄(8.5 g, 40 mmol), and 1,4-dioxane (10 mL) were loaded into athree-necked flask, and the mixture was refluxed under an argonatmosphere for 10 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The resultant sample was purified by columnchromatography. The purified product was concentrated and exsiccated,and was then recrystallized twice, whereby a white powder (Compound No.11) was obtained. The powder was purified by sublimation, whereby awhite solid was obtained in an amount of 2.1 g in 35% yield.

FD-MS C₄₂H₂₄N₂O₂: theoretical value 588, observed value 588

Synthesis Example 3 Synthesis of Compound No. 22

Compound 4 (2.5 g, 6.0 mmol), Compound 7 (2.9 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 22) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.3 g in35% yield.

FD-MS C₄₆H₂₆O₂: theoretical value 610, observed value 610

Synthesis Example 4 Synthesis of Compound No. 28

Compound 4 (2.5 g, 6.0 mmol), Compound 8 (3.8 g, 13.2 mmol), a 2 Maqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 28) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 2.1 g in47% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 5 Synthesis of Compound No. 39 (1) Synthesis ofCompound 9

Compound 4 (10.0 g, 24.0 mmol), phenylboronic acid (6.4 g, 52.8 mmol), a2 M aqueous solution of Na₂CO₃ (48 mL, 96 mmol), DME (48 mL), toluene(48 mL), and Pd[PPh₃]₄ (1.4 g, 1.2 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (300 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 7.5 g in 76% yield.

FD-MS C₃₀H₁₈O₂: theoretical value 410, observed value 410

(2) Synthesis of Compound 10

Compound 9 (7.5 g, 18.3 mmol) and CH₂Cl₂ (100 mL) were loaded into athree-necked flask, and bromine (2.9 g, 18.3 mmol) was dropped to theflask under an Ar atmosphere at 0° C. After that, the mixture wasstirred at room temperature for 8 hours. After the completion of thereaction, the resultant sample was transferred to a separating funnel,and water (50 mL) was charged into the funnel. Then, the mixture wasextracted with CH₂Cl₂. The organic layer was washed with a saturatedaqueous solution of NaNO₂ (50 mL) and dried with MgSO₄, and was thenfiltrated and concentrated. The resultant sample was purified by columnchromatography, whereby a white solid was obtained in an amount of 5.4 gin 60% yield.

FD-MS C₃₀H₁₇BrO₂: theoretical value 489, observed value 489

(3) Synthesis of Compound No. 39

Compound 10 (4.9 g, 10.0 mmol), Compound 8 (3.2 g, 11.0 mmol), a 2 Maqueous solution of Na₂CO₃ (10 mL, 20 mmol), DME (20 mL), toluene (20mL), and Pd[PPh₃]₄ (0.58 g, 0.5 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (100 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography. The purified product wasconcentrated and exsiccated, and was then recrystallized twice, wherebya white powder (Compound No. 39) was obtained. The powder was purifiedby sublimation, whereby a white solid was obtained in an amount of 1.8 gin 28% yield.

FD-MS C₄₈H₂₈O₃: theoretical value 652, observed value 652

Synthesis Example 6 Synthesis of Compound No. 57 (1) Synthesis ofCompound 11

Compound 4 (16.6 g, 40.0 mmol), phenylboronic acid (4.9 g, 40 mmol), a 2M aqueous solution of Na₂CO₃ (40 mL, 80 mmol), DME (80 mL), toluene (80mL), and Pd[PPh₃]₄ (2.3 g, 2.0 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (300 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 10.7 g in 65% yield.

FD-MS C₂₄H₁₃BrO₂: theoretical value 413, observed value 413

(2) Synthesis of Compound 12

Compound 11 (10 g, 24.2 mmol) and THF (240 mL) were loaded into athree-necked flask, and the mixture was cooled to −78° C. Then, n-BuLi(1.65 M solution in n-hexane, 16.1 mL, 26.6 mmol) was added dropwise tothe flask, and the resultant mixture was stirred at −78° C. for 20minutes. Triisopropyl borate (13.7 g, 72.6 mmol) was added to theresultant, and the mixture was stirred at −78° C. for 1 hour. Afterthat, the resultant was left to stand overnight at room temperature.Then, 1 N HCl (100 mL) was charged into the resultant, and the mixturewas stirred at room temperature for 1 hour. The resultant sample wasconcentrated, and was then transferred to a separating funnel. Water(100 mL) was charged into the funnel, and the mixture was extracted withCH₂Cl₂. The extract was dried with MgSO₄, and was then filtrated andconcentrated. The resultant sample was purified by recrystallization(toluene-hexane), whereby a white solid was obtained in an amount of 5.5g in 60% yield.

(3) Synthesis of Compound No. 57

Compound 11 (2.5 g, 6.0 mmol), Compound 12 (2.5 g, 6.6 mmol), a 2 Maqueous solution of Na₂CO₃ (6 mL, 12 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (100 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography. The purified product wasconcentrated and exsiccated, and was then recrystallized twice, wherebya white powder (Compound No. 57) was obtained. The powder was purifiedby sublimation, whereby a white solid was obtained in an amount of 1.6 gin 40% yield.

FD-MS C₄₈H₂₆O₄: theoretical value 666, observed value 666

Synthesis Example 7 Synthesis of Compound No. 58 (1) Synthesis ofCompound 14

Compound 4 (16.6 g, 40 mmol), Compound 13 (8.5 g, 40 mmol), a 2 Maqueous solution of Na₂CO₃ (40 mL, 80 mmol), DME (80 mL), toluene (80mL), and Pd[PPh₃]₄ (2.3 g, 2.0 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (300 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 11.1 g in 55% yield.

FD-MS C₃₀H₁₅BrO₃: theoretical value 503, observed value 503

(2) Synthesis of Compound 15

Compound 14 (11 g, 21.9 mmol) and THF (220 mL) were loaded into athree-necked flask, and the mixture was cooled to −78° C. Then, n-BuLi(1.65 M solution in n-hexane, 14.5 mL, 24.0 mmol) was added dropwise tothe flask, and the resultant mixture was stirred at −78° C. for 20minutes. Triisopropyl borate (12.4 g, 65.6 mmol) was added to theresultant, and the mixture was stirred at −78° C. for 1 hour. Afterthat, the resultant was left to stand overnight at room temperature.Then, 1 N HCl (100 mL) was charged into the resultant, and the mixturewas stirred at room temperature for 1 hour. The resultant sample wasconcentrated, and was then transferred to a separating funnel. Water(100 mL) was charged into the funnel, and the mixture was extracted withCH₂Cl₂. The extract was dried with MgSO₄, and was then filtrated andconcentrated. The resultant sample was purified by recrystallization(toluene-hexane), whereby a white solid was obtained in an amount of 6.4g in 62% yield.

(3) Synthesis of Compound No. 58

Compound 14 (3.0 g, 6.0 mmol), Compound 15 (3.1 g, 6.6 mmol), a 2 Maqueous solution of Na₂CO₃ (6 mL, 12 mmol), DME (12 mL), toluene (12mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into a three-neckedflask, and the mixture was refluxed under an Ar atmosphere for 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (100 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography. The purified product wasconcentrated and exsiccated, and was then recrystallized twice, wherebya white powder (Compound No. 58) was obtained. The powder was purifiedby sublimation, whereby a white solid was obtained in an amount of 1.3 gin 26% yield.

FD-MS C₆₀H₃₀O₆: theoretical value 846, observed value 846

Synthesis Example 8 Synthesis of Compound No. 60

Compound 12 (5.5 g, 14.5 mmol), 1,3-dibromobenzene (1.7 g, 7.3 mmol), a2 M aqueous solution of Na₂CO₃ (15 mL, 30 mmol), DME (15 mL), toluene(15 mL), and Pd[PPh₃]₄ (0.42 g, 0.37 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 60) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.6 g in29% yield.

FD-MS C₅₄H₃₀O₄: theoretical value 742, observed value 742

Synthesis Example 9 Synthesis of Compound No. 62

Compound 12 (8.3 g, 21.9 mmol), 1,3,5-tribromobenzene (2.3 g, 7.3 mmol),a 2 M aqueous solution of Na₂CO₃ (22.5 mL, 45 mmol), DME (15 mL),toluene (15 mL), and Pd[PPh₃]₄ (0.63 g, 0.56 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (150 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography. The purified product wasconcentrated and exsiccated, and was then recrystallized twice, wherebya white powder (Compound No. 62) was obtained. The powder was purifiedby sublimation, whereby a white solid was obtained in an amount of 1.1 gin 14% yield.

FD-MS C₇₈H₄₂O₆: theoretical value 1075, observed value 1075

Synthesis Example 10 Synthesis of Compound No. 20

Compound 4 (2.5 g, 6.0 mmol), 3-biphenylboronic acid (2.6 g, 13.2 mmol),a 2 M aqueous solution of Na₂CO₃ (12 mL, 24 mmol), DME (12 mL), toluene(12 mL), and Pd[PPh₃]₄ (0.35 g, 0.3 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (50 mL) was charged into the funnel. Then, the mixturewas extracted with CH₂Cl₂. The extract was dried with MgSO₄, and wasthen filtrated and concentrated. The resultant sample was purified bysilica gel column chromatography. The purified product was concentratedand exsiccated, and was then recrystallized twice, whereby a whitepowder (Compound No. 20) was obtained. The powder was purified bysublimation, whereby a white solid was obtained in an amount of 1.3 g in39% yield.

FD-MS C₄₂H₂₆O₂: theoretical value 562, observed value 562

Synthesis Example 11 Synthesis of Compound No. 67 (1) Synthesis ofCompound 17

1,4-dibromo-2,5-difluorobenzene (5.4 g, 20.0 mmol), Compound 16 (12.8 g,42.0 mmol), a 2 M aqueous solution of Na₂CO₃ (40 mL, 80.0 mmol), DME (40mL), toluene (40 mL), and Pd[PPh₃]₄ (1.2 g, 1.0 mmol) were loaded into athree-necked flask, and the mixture was refluxed under an Ar atmospherefor 8 hours.

After the completion of the reaction, the resultant was cooled to roomtemperature. The resultant sample was transferred to a separatingfunnel, and water (100 mL) was charged into the funnel. Then, themixture was extracted with CH₂Cl₂. The extract was dried with MgSO₄, andwas then filtrated and concentrated. The resultant sample was purifiedby silica gel column chromatography, whereby a white solid was obtainedin an amount of 8.8 g in 70% yield. FD-MS C₄₄H₃₂F₂O₂: theoretical value630, observed value 630

(2) Synthesis of Compound 18

Compound 17 (8.8 g, 14.0 mmol), a 1 M solution of BBr₃ in CH₂Cl₂ (34 mL,34.0 mmol), and CH₂Cl₂ (140 mL) were loaded into a three-necked flask,and the mixture was stirred under an Ar atmosphere at 0° C. for 8 hours.After that, the mixture was left to stand at room temperature overnight.After the completion of the reaction, the resultant was neutralized witha saturated aqueous solution of NaHCO₃. The resultant sample wastransferred to a separating funnel, and was extracted with CH₂Cl₂. Theresultant sample was purified by silica gel column chromatography,whereby a white solid was obtained in an amount of 7.8 g in 93% yield.FD-MS C₄₂H₂₈F₂O₂: theoretical value 602, observed value 602

(3) Synthesis of Compound No. 67

Compound 18 (7.8 g, 12.9 mmol), K₂CO₃ (7.2 g, 51.8 mmol), and NMP (50mL) were loaded into a three-necked flask, and the mixture was stirredunder an Ar atmosphere at 200° C. for 3 hours. After the completion ofthe reaction, the resultant was cooled to room temperature. Toluene (500mL) was charged into the resultant sample. The mixture was transferredto a separating funnel, and was washed with water. The washed productwas dried with MgSO₄, and was then filtrated and concentrated. Theresultant sample was purified by silica gel column chromatography. Thepurified product was concentrated and exsiccated, and was thenrecrystallized twice, whereby a white powder (Compound No. 67) wasobtained. The powder was purified by sublimation, whereby a white solidwas obtained in an amount of 2.5 g in 35% yield.

FD-MS C₄₂H₂₆O₂: theoretical value 562, observed value 562

An apparatus and measurement conditions adopted for field desorptionmass spectrometry (FD-MS) in each of Synthesis Examples 1 to 11 areshown below.

Apparatus: HX110 (manufactured by JEOL Ltd.)

Conditions:

-   -   accelerating voltage 8 kV    -   scan range m/z=50 to 1,500    -   emitter kind: carbon    -   emitter current: 0 mA→2 mA/min→40 mA (held for 10 minutes)

Example 1 Production of Organic EL Device

A glass substrate provided with an ITO transparent electrode measuring25 mm by 75 mm by 1.1 mm (manufactured by GEOMATEC Co., Ltd.) wassubjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes.Further, the substrate was subjected to ultraviolet (UV)-ozone cleaningfor 30 minutes.

The glass substrate provided with a transparent electrode thus cleanedwas mounted on a substrate holder of a vacuum deposition apparatus.First, Compound A was deposited from the vapor onto the surface of theglass substrate on the side where a transparent electrode line wasformed so as to cover the transparent electrode, whereby a holetransporting layer having a thickness of 30 nm was obtained.

Compound No. 1 as a host for phosphorescence and Ir(Ph-ppy)₃ as a dopantfor phosphorescence were co-deposited from the vapor onto the holetransporting layer, whereby a phosphorescent layer having a thickness of30 nm was obtained. The concentration of Ir(Ph-ppy)₃ was 5 mass %.

Subsequently, Compound B having a thickness of 10 nm, Compound C havinga thickness of 20 nm, LiF having a thickness of 1 nm, and metal Alhaving a thickness of 80 nm were sequentially laminated on thephosphorescent layer, whereby a cathode was obtained. It should be notedthat LiF as an electron injectable electrode was formed at a rate of 1Å/min.

(Evaluation of Organic EL Device for Light Emitting Performance)

The organic EL device thus produced was caused to emit light by beingdriven with a direct current. The luminance (L) of the emitted light andthe current density at which the device started to emit the light weremeasured. Then, the current efficiency (L/J) of the device at aluminance of 1,000 cd/m² was determined. Further, the lifetime of thedevice at a luminance of 20,000 cd/m² was determined. Table 1 shows theresults.

Examples 2 to 9

Organic EL devices were each produced in the same manner as in Example 1except that a host material listed in Table 1 was used instead of HostCompound No. 1 in Example 1, and the devices were each evaluated in thesame manner as in Example 1. Table 1 shows the results of the evaluationfor light emitting performance.

Comparative Examples 1 and 2

Organic EL devices were each produced in the same manner as in Example 1except that the following compound (a) or (b) described in EP 0908787 Awas used as a host material instead of Host Compound No. 1 in Example 1,and the devices were each evaluated in the same manner as in Example 1.Table 1 shows the results of the evaluation for light emittingperformance.

Comparative Examples 3 and 4

Organic EL devices were each produced in the same manner as in Example 1except that the following compound (c) or (d) described in WO2006-122630 was used as a host material instead of Host Compound No. 1in Example 1, and the devices were each evaluated in the same manner asin Example 1. Table 1 shows the results of the evaluation for lightemitting performance.

Comparative Example 5

An organic EL device was produced in the same manner as in Example 1except that the following compound (e) described in WO 2007-063754 wasused as a host material instead of Host Compound No. 1 in Example 1, andthe device was evaluated in the same manner as in Example 1. Table 1shows the results of the evaluation for light emitting performance.

Comparative Example 6

An organic EL device was produced in the same manner as in Example 1except that the following compound (f) described in JP 2008-81494 A wasused as a host material instead of Host Compound No. 1 in Example 1, andthe device was evaluated in the same manner as in Example 1. Table 1shows the results of the evaluation for light emitting performance.

Comparative Example 7

An organic EL device was produced in the same manner as in Example 1except that the following compound (g) described in US 2002-0132134 Aand US 2003-0044646 A was used as a host material instead of HostCompound No. 1 in Example 1, and the device was evaluated in the samemanner as in Example 1. Table 1 shows the results of the evaluation forlight emitting performance.

TABLE 1 Voltage (V) Efficiency Lifetime (hr) Host @ 20 (cd/A) @ 1,000 @20,000 Compound mA/cm² cd/m² cd/m² Example 1  (1) 5.8 52.3 350 Example 2(11) 4.5 45.8 110 Example 3 (22) 6.0 50.8 320 Example 4 (28) 5.2 57.6400 Example 5 (39) 5.3 57.5 300 Example 6 (57) 5.2 56.8 410 Example 7(58) 5.0 50.5 350 Example 8 (60) 5.4 57.8 370 Example 9 (62) 5.3 54.3500 Comparative (a) 4.6 26.5 50 Example 1 Comparative (b) 4.2 17.6 30Example 2 Comparative (c) 4.9 37.5 50 Example 3 Comparative (d) 4.7 35.960 Example 4 Comparative (e) 4.3 17.3 30 Example 5 Comparative (f) 5.538.2 50 Example 6 Comparative (g) 5.4 28.7 60 Example 7

Example 10 Production of Organic EL Device

The glass substrate provided with a transparent electrode cleaned in thesame manner as described above was mounted on a substrate holder of avacuum deposition apparatus. First, Compound A was deposited from thevapor onto the surface of the glass substrate on the side where atransparent electrode line was formed so as to cover the transparentelectrode, whereby a hole transporting layer having a thickness of 30 nmwas obtained.

Compound No. 198 as a host for phosphorescence and Ir(Ph-ppy)₃ as adopant for phosphorescence were co-deposited from the vapor onto thehole transporting layer, whereby a phosphorescent layer having athickness of 30 nm was obtained. The concentration of Ir(Ph-ppy)₃ was 10mass %.

Subsequently, Compound No. 20 having a thickness of 10 nm, Compound Chaving a thickness of 20 nm, LiF having a thickness of 1 nm, and metalAl having a thickness of 80 nm were sequentially laminated on thephosphorescent layer, whereby a cathode was obtained. It should be notedthat LiF as an electron injectable electrode was formed at a rate of 1Å/min.

(Evaluation of Organic EL Device for Light Emitting Performance)

The organic EL device thus produced was caused to emit light by beingdriven with a direct current. The luminance (L) of the emitted light andthe current density at which the device started to emit the light weremeasured. Then, the current efficiency (L/J) of the device at aluminance of 1,000 cd/m² was determined. Further, the lifetime of thedevice at a luminance of 20,000 cd/m² was determined. Table 2 shows theresults.

Examples 11 to 16

Organic EL devices were each produced in the same manner as in Example10 except that a host compound and an electron transportable compoundlisted in Table 2 were used instead of Host Compound No. 198 andElectron Transportable Compound No. 20 in Example 10, and the deviceswere each evaluated in the same manner as in Example 10. Table 2 showsthe results of the evaluation for light emitting performance.

Comparative Example 8

An organic EL device was produced in the same manner as in Example 10except that: CBP was used instead of Host Compound No. 198 in Example10; and BAlq was used instead of Electron Transportable Compound No. 20in Example 10. Then, the device was evaluated in the same manner as inExample 10. Table 2 shows the results of the evaluation for lightemitting performance.

TABLE 2 Electron Efficiency Host Transport- Voltage (V) (cd/A) Lifetime(hr) Com- able @ 20 @ 1,000 @ 20,000 pound Compound mA/cm² cd/m² cd/m²Example 10 (198) (20) 4.7 65.1 500 Example 11 (198) (67) 4.5 63.9 550Example 12 (137) (67) 4.5 57.1 350 Example 13 (193) (67) 5.2 61.8 400Example 14 (209) (67) 5.3 63.8 380 Example 15 CBP (20) 5.3 47.2 100Example 16 CBP (67) 5.1 48.5 100 Comparative CBP BAlq 6.5 45.1 30Example 8

Each of the organic EL devices of the comparative examples showed alower current efficiency, was driven at a higher voltage, and had ashorter lifetime than those of each of the organic EL devices of theexamples.

INDUSTRIAL APPLICABILITY

As described above in detail, the utilization of the material for anorganic EL device of the present invention can provide an organic ELdevice which: shows high luminous efficiency; is free of any pixeldefect; and has a long lifetime. Accordingly, the organic EL device ofthe present invention is extremely useful as, for example, a lightsource for various electronic instruments. In addition, the material canbe effectively used also as a material for an organic electron device,and is extremely useful in an organic solar cell, organic semiconductorlaser, a sensor using organic matter, or an organic TFT.

1. A material for an organic electroluminescence device represented byone of formulae (1) and (2):

wherein: X₁ and X₂ each independently represent O, N—R₁, or CR₂R₃,provided that a case where both X₁ and X₂ represent CR₂R₃ is excluded;R₁, R₂, and R₃ each independently represent an alkyl group having 1 to20 carbon atoms, a substituted or unsubstituted cycloalkyl group havinga ring formed of 3 to 20 carbon atoms, an aralkyl group having 7 to 24carbon atoms, a silyl group having 3 to 20 carbon atoms, a substitutedor unsubstituted aromatic hydrocarbon group having a ring formed of 6 to24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclicgroup having a ring formed of 3 to 24 atoms, provided that, when both X₁and X₂ represent N—R₁, at least one R₁ represents a residue ofdibenzofuran, dibenzothiophene, phenoxazine, phenothiazine,dihydroacridine or N-methylbenzimidazole, wherein the residue isoptionally substituted by a substituent selected from the groupconsisting of an alkyl group having 1 to 10 carbon atoms, a cycloalkylgroup having a ring formed of 3 to 40 carbon atoms, an alkoxy grouphaving 1 to 6 carbon atoms, a cycloalkoxy group having a ring formed of3 to 10 carbon atoms, an aromatic hydrocarbon group having a ring formedof 6 to 40 carbon atoms, an amino group substituted with an aromatichydrocarbon group having a ring formed of 6 to 40 carbon atoms, an estergroup having an aromatic hydrocarbon group having a ring formed of 6 to40 carbon atoms, an ester group having an alkyl group having 1 to 6carbon atoms, cyano group, nitro group, and halogen atom; n represents2, 3, or 4, and the material represented by the formula (2) comprises adimer using L₃ as a linking group for n=2, a trimer using L₃ as alinking group for n=3, or a tetramer using L₃ as a linking group forn=4; L₁ represents a single bond, an alkyl or alkylene group having 1 to20 carbon atoms, a substituted or unsubstituted cycloalkyl orcycloalkylene group having a ring formed of 3 to 20 carbon atoms, amonovalent or divalent silyl group having 2 to 20 carbon atoms, asubstituted or unsubstituted, monovalent or divalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond; L₂ representsa single bond, an alkyl or alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl or cycloalkylene group having aring formed of 3 to 20 carbon atoms, a monovalent or divalent silylgroup having 2 to 20 carbon atoms, a substituted or unsubstituted,monovalent or divalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, monovalentor divalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with a benzene ring c through acarbon-carbon bond; when n represents 2, L₃ represents a single bond, analkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkylene group having a ring formed of 3 to 20 carbonatoms, a divalent silyl group having 2 to 20 carbon atoms, a substitutedor unsubstituted, divalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,divalent aromatic heterocyclic group which has a ring formed of 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, when n represents 3, L₃ represents a trivalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, atrivalent silyl group having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalentaromatic heterocyclic group which has 3 to 24 atoms and which is linkedwith the benzene ring c through a carbon-carbon bond, or when nrepresents 4, L₃ represents a tetravalent alkane having 1 to 20 carbonatoms, a substituted or unsubstituted, tetravalent cycloalkane having aring formed of 3 to 20 carbon atoms, a silicon atom, a substituted orunsubstituted, tetravalent aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstituted,tetravalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with the benzene ring c through acarbon-carbon bond; A₁ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₁ through a carbon-carbonbond, provided that, when L₁ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₁ represents a hydrogen atomis excluded; A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when X₁ and X₂ each represent O or CR₂R₃ and both L₁and L₂ represent single bonds, a case where A₁ and A₂ simultaneouslyrepresent hydrogen atoms is excluded; the substituent of A₁ and A₂ isselected from the group consisting of an alkyl group having 1 to 10carbon atoms, a cycloalkyl group having a ring formed of 3 to 40 carbonatoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkoxy grouphaving a ring formed of 3 to 10 carbon atoms, an aromatic hydrocarbongroup having a ring formed of 6 to 40 carbon atoms, an aromaticheterocyclic group having a ring formed of 3 to 40 atoms, an amino groupsubstituted with an aromatic hydrocarbon group having a ring formed of 6to 40 carbon atoms, an ester group having an aromatic hydrocarbon grouphaving a ring formed of 6 to 40 carbon atoms, an ester group having analkyl group having 1 to 6 carbon atoms, cyano group, nitro group, andhalogen atom; Y₁, Y₂, and Y₃ each represent an alkyl group having 1 to20 carbon atoms, a substituted or unsubstituted cycloalkyl group havinga ring formed of 3 to 20 carbon atoms, an alkoxy group having 1 to 20carbon atoms, an aralkyl group having 7 to 24 carbon atoms, a silylgroup having 3 to 20 carbon atoms, a substituted or unsubstitutedaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted aromatic heterocyclic group which hasa ring formed of 3 to 24 atoms and which is linked with the benzene ringa, b, or c through a carbon-carbon bond, a number of each of Y₁ and Y₃is 0, 1, 2, or 3, and a number of Y₂ is 0, 1, or 2; and A₁, A₂, L₁, L₂,and L₃ are each free of any carbonyl group.
 2. The material for anorganic electroluminescence device according to claim 1, wherein thematerial for an organic electroluminescence device is represented by anyone of formulae (3) to (10):

wherein R₁, R₂, R₃, n, L₁, L₂, L₃, A₁, A₂, Y₁, Y₂, and Y₃ are as definedin claim
 1. 3-8. (canceled)
 9. An organic electroluminescence devicecomprising one or more organic thin film layers including a lightemitting layer between a cathode and an anode, wherein at least onelayer of the organic thin film layers comprises the material for anorganic electroluminescence device according to claim
 1. 10. The organicelectroluminescence device according to claim 9, wherein the lightemitting layer comprises the material for an organic electroluminescencedevice as a host material.
 11. The organic electroluminescence deviceaccording to claim 9, wherein the light emitting layer further comprisesa phosphorescent material.
 12. The organic electroluminescence deviceaccording to claim 9, wherein the light emitting layer comprises a hostmaterial and a phosphorescent material, and the phosphorescent materialcomprises an orthometalated complex of an iridium (Ir), osmium (Os), orplatinum (Pt) metal.
 13. The organic electroluminescence deviceaccording to claim 9, further comprising an electron injecting layerbetween the light emitting layer and the cathode, wherein the electroninjecting layer comprises a nitrogen-containing ring derivative. 14.(canceled)
 15. The organic electroluminescence device according to claim9, wherein the light emitting layer comprises, as a host material, amaterial for an organic electroluminescence device serving as a compoundhaving a n-conjugated heteroacene skeleton crosslinked with a carbonatom, nitrogen atom, oxygen atom, or sulfur atom.
 16. The organicelectroluminescence device according to claim 9, wherein the lightemitting layer comprises a material for an organic electroluminescencedevice represented by any one of formulae (15) to (18) as a hostmaterial:

wherein: X₃, X₄, X₅, and X₆ each independently represent O, S, N—R₁, orCR₂R₃; R₁, R₂, and R₃ each independently represent an alkyl group having1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving a ring formed of 3 to 20 carbon atoms, an aralkyl group having 7to 24 carbon atoms, a silyl group having 3 to 20 carbon atoms, asubstituted or unsubstituted aromatic hydrocarbon group having a ringformed of 6 to 24 carbon atoms, or a substituted or unsubstitutedaromatic heterocyclic group having a ring formed of 3 to 24 atoms,provided that, when both X₃ and X₄, or both X₅ and X₆, represent N—R₁,at least one R₁ represents a substituted or unsubstituted, monovalentfused aromatic heterocyclic group having a ring formed of 8 to 24 atoms;n represents 2, 3, or 4, and the material represented by one of theformulae (16) and (18) comprises a dimer using L₃ as a linking group forn=2, a trimer using L₃ as a linking group for n=3, or a tetramer usingL₃ as a linking group for n=4; L₁ represents a single bond, an alkyl oralkylene group having 1 to 20 carbon atoms, a substituted orunsubstituted cycloalkyl or cycloalkylene group having a ring formed of3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to20 carbon atoms, a substituted or unsubstituted, monovalent or divalentaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted, monovalent or divalent aromaticheterocyclic group which has a ring formed of 3 to 24 atoms and which islinked with a benzene ring a through a carbon-carbon bond; L₂ representsa single bond, an alkyl or alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl or cycloalkylene group having aring formed of 3 to 20 carbon atoms, a monovalent or divalent silylgroup having 2 to 20 carbon atoms, a substituted or unsubstituted,monovalent or divalent aromatic hydrocarbon group having a ring formedof 6 to 24 carbon atoms, or a substituted or unsubstituted, monovalentor divalent aromatic heterocyclic group which has a ring formed of 3 to24 atoms and which is linked with a benzene ring c through acarbon-carbon bond, provided that, when both X₇ and X₈, both X₉ and X₁₀,or both X₁₁ and X₁₂, represent CR₂R₃ and both L₁ and L₂ representsubstituted or unsubstituted, monovalent or divalent aromatichydrocarbon groups having a ring formed of 6 to 24 carbon atoms, a casewhere L₁ and L₂ are simultaneously linked at para positions with respectto a benzene ring b is excluded; when n represents 2, L₃ represents asingle bond, an alkylene group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkylene group having a ring formed of3 to 20 carbon atoms, a divalent silyl group having 2 to 20 carbonatoms, a substituted or unsubstituted, divalent aromatic hydrocarbongroup having a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, divalent aromatic heterocyclic group which has a ringformed of 3 to 24 atoms and which is linked with the benzene ring cthrough a carbon-carbon bond, when n represents 3, L₃ represents atrivalent alkane having 1 to 20 carbon atoms, a substituted orunsubstituted, trivalent cycloalkane having a ring formed of 3 to 20carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted, trivalent aromatic hydrocarbon grouphaving a ring formed of 6 to 24 carbon atoms, or a substituted orunsubstituted, trivalent aromatic heterocyclic group which has 3 to 24atoms and which is linked with the benzene ring c through acarbon-carbon bond, or when n represents 4, L₃ represents a tetravalentalkane having 1 to 20 carbon atoms, a substituted or unsubstituted,tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, asilicon atom, a substituted or unsubstituted, tetravalent aromatichydrocarbon group having a ring formed of 6 to 24 carbon atoms, or asubstituted or unsubstituted, tetravalent aromatic heterocyclic groupwhich has a ring formed of 3 to 24 atoms and which is linked with thebenzene ring c through a carbon-carbon bond, provided that, when both X₇and X₈, both X₉ and X₁₀, or both X₁₁ and X₁₂, represent CR₂R₃ and bothL₁ and L₃ represent a substituted or unsubstituted, monovalent,divalent, trivalent, or tetravalent aromatic hydrocarbon group having aring formed of 6 to 24 carbon atoms, a case where L₁ and L₃ aresimultaneously linked at para positions with respect to the benzene ringb is excluded; A₁ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₁ through a carbon-carbonbond, provided that, when L₁ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₁ represents a hydrogen atomis excluded; A₂ represents a hydrogen atom, a substituted orunsubstituted cycloalkyl group having a ring formed of 3 to 20 carbonatoms, a silyl group having 3 to 20 carbon atoms, a substituted orunsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24carbon atoms, or an aromatic heterocyclic group which has a ring formedof 3 to 24 atoms and which is linked with L₂ through a carbon-carbonbond, provided that, when L₂ represents an alkyl or alkylene grouphaving 1 to 20 carbon atoms, a case where A₂ represents a hydrogen atomis excluded, and, when X₇ and X₈, X₉ and X₁₀, or X₁₁ and X₁₂, eachrepresent O, S, or CR₂R₃ and both L₁ and L₂ represent single bonds, acase where A₁ and A₂ simultaneously represent hydrogen atoms isexcluded; Y₁, Y₂, and Y₃ each represent an alkyl group having 1 to 20carbon atoms, a substituted or unsubstituted cycloalkyl group having aring formed of 3 to 20 carbon atoms, an alkoxy group having 1 to 20carbon atoms, an aralkyl group having 7 to 24 carbon atoms, a silylgroup having 3 to 20 carbon atoms, a substituted or unsubstitutedaromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms,or a substituted or unsubstituted aromatic heterocyclic group which hasa ring formed of 3 to 24 atoms and which is linked with the benzene ringa, b, or c through a carbon-carbon bond, a number of each of Y₁ and Y₃is 0, 1, 2, or 3, and a number of Y₂ is 0, 1, or 2; and A₁, A₂, L₁, L₂,and L₃ are each free of any carbonyl group.
 17. The organicelectroluminescence device according to claim 16, wherein the materialfor an organic electroluminescence device in the light emitting layer isrepresented by any one of formulae (19) to (22) as a host material:

wherein n, L₁, L₂, L₃, A₁, A₂, Y₁, Y₂, and Y₃ are as defined in claim16.
 18. The organic electroluminescence device according to claim 9,further comprising a hole transporting layer between the light emittinglayer and the anode, wherein the hole transporting layer comprises thematerial for an organic electroluminescence device.
 19. The organicelectroluminescence device according to claim 9, further comprising areducing dopant at an interfacial region between the cathode and theorganic thin film layers.